CN106883153B - A kind of preparation method of two amphyls of 2- sulfonyls -1,4- - Google Patents
A kind of preparation method of two amphyls of 2- sulfonyls -1,4- Download PDFInfo
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- CN106883153B CN106883153B CN201710230493.1A CN201710230493A CN106883153B CN 106883153 B CN106883153 B CN 106883153B CN 201710230493 A CN201710230493 A CN 201710230493A CN 106883153 B CN106883153 B CN 106883153B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/06—Separation; Purification; Stabilisation; Use of additives
Abstract
The invention discloses a kind of preparation methods of 2- sulfonyls-- two amphyl of Isosorbide-5-Nitrae (I), belong to organic chemistry filed.This method is using benzoquinones, substitution benzoquinones or naphthoquinones, substitution naphthoquinones and substituted sulfinic acid sodium as raw material, in NH4Under I effects, 2- sulfonyls-- two amphyl of Isosorbide-5-Nitrae is obtained by the reaction in methanol solvate.
Description
Technical field
The present invention relates to a kind of preparation methods of 2- sulfonyls-- two amphyl of Isosorbide-5-Nitrae, belong to organic synthesis field.
Background technology
Aryl compound is important industrial chemicals and medicine intermediate.Phenylsulfone compounds are natural products and drug
The basic component units of object are closed, derivative has potentially to the inhibiting effect of enzyme and virus.2- sulfonyl -1,4- diphenol is
The important derivatives of the quinones containing sulfonyl have the bioactivity such as anticancer, antimycotic, antitumor, especially have to FabH enzymes latent
Inhibiting effect.It is to have in organic synthesis, functional material and pharmacology due to its unique physical property and bioactivity
The molecule construction module of value, all containing this important structure in many drug molecules.Therefore, synthetic method for a long time with
Constantly it is valued by people.
Currently, being combined to 2- sulfonyls-- two amphyl of Isosorbide-5-Nitrae mainly by two kinds of methods by the direct sulphonyl of quinones：
(1) C-S keys are formed using transition metal-catalyzed direct function dough, such as to replace naphthoquinones with substituted phenylsulfonyl chloride as raw material,
Under metal Pd, Ir and Ag catalysis, 2- benzenesulfonyl naphthoquinone derivatives are synthesized；Then NaBH is used4Reduction obtains the 2- sulphonyl of series
Two amphyls of base -1,4- (a routes) (Ge BY, Wang DW, Dong WF, Ma PM, Li YL, Ding YQ,
Tetrahedron Lett.,2014,55,5443-5446；Wang L,Xie,YB,Yang QL,Liu MG,Zheng KB,Hu
YL,Huang NY,J Iran Chem Soc.,2016,13,1797-1803.)；This synthetic method needs two steps to react
At reaction needs toxic and expensive metallic catalyst, while requiring alkaline environment.(2) pass through nonmetal catalyzed direct function
Dough realizes the sulfonylation to quinones, such as with ionic liquid ([bmim] BF4) be solvent and catalyst, substitution quinones with
Two amphyls (b routes) of benzenesulfinic acid reaction synthesis 2- sulfonyls -1,4- (Yadav JS, Reddy BVS, Swamy T,
Ramireddy N,Synthesis,2004,2004,1849-1853)；The raw material benzenesulfinic acid that the reaction needs is expensive,
And be oxidized easily in air, lyate ion liquid used post-processing is cumbersome.For another example, it is catalysis with trifluoroacetic acid
Agent, in the in the mixed solvent of dichloromethane and water, substitution quinones reacts synthesis 2- sulfonyls-Isosorbide-5-Nitrae-diphenol with benzene sulfinic acid sodium salt and spreads out
Biological (c routes) (Alhamadsheh MM, Waters NC, Sachdeva S, Lee P, Reynold KA,
Bioorg.Med.Chem.Lett.,2008,18,6402-6405；Bruce JM,Lloyd-Williams P,
J.Chem.Soc.,Perkin Trans.1,1992,21,2877-2884).This method needs under the conditions of strong acid trifluoroacetic acid
It carries out, the restricted application of substrate, and reaction unit is required high.
As seen from the above, it is anti-to be catalyzed to be generally needed to be added strong acid, highly basic or metallic catalyst for traditional synthetic method
It answers, costly, reaction condition is harsher, and the reaction time is long for substrate or catalyst price, substrate restricted application etc..This
For large-scale industrial production, generally requiring equipment has higher anti-corrosion capability, and is examined from the angle of environmental protection
Consider, is not very ideal.Therefore, find that reaction condition is mild, high income, it is at low cost and meet Green Chemistry and require to have
The approach of effect synthesis 2- sulfonyls-Isosorbide-5-Nitrae-diphenol just becomes the target that researcher pursues all the time.
Invention content
Based on the studies above background, cheap, mild condition that the purpose of the present invention is to provide a kind of raw materials, it is environmentally protective and
High income obtains the new synthetic method of 2- sulfonyls-- two amphyl of Isosorbide-5-Nitrae by single step reaction.
The purpose of the invention is achieved by the following technical solution：
One kind 2- sulfonyls-- two amphyl of Isosorbide-5-Nitrae, structure are indicated with following formula (I)s：
In formula, R1Represent following group：Hydrogen-based, methyl, ethyl, methoxyl group or halogen；R2Represent following group：Hydrogen-based, first
Base, ethyl, methoxyl group, ethyoxyl, nitro, amino, hydroxyl, acetoxyl group or halogen；R3Represent following group：Methyl, ethyl,
Cyclopropyl, phenyl, p-methylphenyl, to ethylbenzene, to tert-butyl-phenyl, p-methoxyphenyl, p-nitrophenyl, to cyano benzene
Base, to halogen phenyl or naphthyl.
It is preferred that：R1Represent following group：Hydrogen-based, methyl, ethyl, methoxyl group etc.；R2Represent following group：Hydrogen-based, methyl,
Methoxyl group, halogen etc.；R3Represent following group：Phenyl, p-methylphenyl, to tert-butyl-phenyl, p-methoxyphenyl, p-nitrophenyl
Base, to cyano-phenyl, to halobenzene base.
The preparation method of above-mentioned 2- sulfonyls-- two amphyl of Isosorbide-5-Nitrae, includes the following steps：
Benzoquinones, substitution benzoquinones or naphthoquinones, substitution naphthoquinones and substituted sulfinic acid sodium are dissolved in solvent, ammonium iodide (NH4I)
For adjuvant, heating reaction after reaction by pillar layer separation, or carries out recrystallizing isolated 2- sulfonyls-Isosorbide-5-Nitrae-
Two amphyls (I).
The benzoquinones, substitution benzoquinones or naphthoquinones, substitution naphthoquinones and the molar ratio of substituted sulfinic acid sodium and ammonium iodide are selected
1:1~2:2~4, preferably 1:2:4.
The reaction dissolvent is dioxane, tetrahydrofuran, dimethyl sulfoxide, n,N-Dimethylformamide, methanol, ethyl alcohol
In it is one or more, preferably methanol be reaction dissolvent.
The reaction temperature is 20-40 DEG C, and preferably 40 DEG C, the reaction time is 0.5-2.0 hours.
The synthetic route of the present invention is as follows：
R in formula1、R2And R3Statement is same as above.
The separation, purification process：(1) reaction solution is depressurized into lower removing solvent, suitable quantity of water is added into raffinate, uses second
Acetoacetic ester extracts three times, and the brine It of extract liquor saturation is primary.Extract liquor passes through column chromatography point after drying, concentration
From purification, yield 90-96%；Or the above-mentioned extract liquor after the brine It of saturation is poured into ice water and is stirred by (2), analysis
Go out solid, is then allowed to stand suction filtration, is recrystallized again with organic solvent after filter cake is dried, yield 80-85%.
Agents useful for same of the present invention is commercially available.
The principle of the invention is the nucleophilic addition that quinone occurs with benzene sulfinic acid sodium salt：Benzene sulfinic acid sodium salt A passes through isomerization shape
At benzenesulfonyl anion B；Benzenesulfonyl anion B is generated intermediate by 2 carbon atoms of nucleophilic addition attack benzoquinones
Body carbanion C；Intermediate C obtains intermediate negative oxygen ion D by isomerization；D is obtained by the tautomerism of ketone and enol
Intermediate E；Target product F is obtained by the reaction in the decomposition product HI of intermediate E and ammonium iodide.
Advantageous effect of the present invention is：The synthetic method raw material of 2- sulfonyls of the present invention-- two amphyl of Isosorbide-5-Nitrae is inexpensively easy
, object is obtained by single step reaction, reaction condition is mild, easy to operate, yield is high, up to 90% or more.It is environmentally protective to have
Conducive to industrialized production, a new way is provided to prepare 2- sulfonyls-- two amphyl of Isosorbide-5-Nitrae with function affect
Diameter.
Specific implementation mode
Below by embodiment, the present invention will be further elaborated, but is not meant to that present disclosure is confined to
Embodiment.
Embodiment 1.R1=R2=-H, R3=-p-OCH3-C6H4When, 2- derives MethOxybenzenesulfonyl benzene-Isosorbide-5-Nitrae-diphenol
The preparation of object
In 50mL round-bottomed flasks be added 1,4-benzoquinone (0.5mmol, 54mg) and to methoxy benzenesulfonic acid sodium (1.0mmol,
194mg), it adds that ammonium iodide (2.0mmol, 290mg) is adjuvant and 10mL methanol is solvent, reacts 2.0h at 40 DEG C；
After reaction, solvent is removed under reduced pressure, 10mL water is added into raffinate, secondary with the extraction of 15mL ethyl acetate, extract liquor is used full
The brine It of sum is primary；Extract liquor anhydrous Na2SO4It is dry, pass through column chromatography (eluant, eluent after reduced pressure：Acetic acid second
Ester/petroleum ether=1/5) separating-purifying, obtain yellow, viscous liquid 0.133g, yield 95.0%.
Colorless solid, mp 188-189 DEG C1H NMR(400MHz,DMSO)δ:9.90(bs,1H),9.39(bs,1H),
7.85(d,JH-H=8.9Hz, 2H), 7.34 (d, JH-H=3.0Hz, 1H), 7.08 (d, JH-H=8.9Hz, 2H), 6.91 (dd, JH-H
=8.8Hz, JH-H=3.0Hz, 1H), 6.75 (d, JH-H=8.8Hz, 1H), 3.79 (s, 3H)13C NMR(100MHz,DMSO)δ:
167.9,154.6,153.2,138.0,135.4(CH),132.0,127.7(CH),123.7(CH),119.2(CH),118.9
(CH),60.8(CH3).HR MS(ESI)m/z:281.0478[M+H]+(calcd for C13H13ClO5S+281.0478).
Embodiment 2.R1=R2=-H, R3=-p-Br-C6H4When, the system of 2- brosyls benzene-- two amphyl of Isosorbide-5-Nitrae
It is standby
In 50mL round-bottomed flasks be added 1,4-benzoquinone (0.5mmol, 54mg) and to bromo-benzene sulfonic acid sodium (1.0mmol,
242mg), it adds that ammonium iodide (2.0mmol, 290mg) is adjuvant and 10mL ethyl alcohol is solvent, reacts 2.0h at 20 DEG C；
After reaction, solvent is removed under reduced pressure, 10mL water is added into raffinate, secondary with the extraction of 15mL ethyl acetate, extract liquor is used full
The brine It of sum is primary；Extract liquor anhydrous Na2SO4It is dry, pass through column chromatography (eluant, eluent after reduced pressure：Acetic acid second
Ester/petroleum ether=1/5) separating-purifying, obtain yellow, viscous liquid 0.150g, yield 92.0%.
Colorless solid, mp 210-211 DEG C1H NMR(400MHz,DMSO)δ:10.07(bs,1H),9.46(bs,1H),
7.83(d,JH-H=8.7Hz, 2H), 7.76 (d, JH-H=8.7Hz, 2H), 7.38 (d, JH-H=3.0Hz, 1H), 6.97 (dd, JH-H
=8.8Hz, JH-H=3.0Hz, 1H), 6.79 (d, JH-H=8.8Hz, 1H)13C NMR(100MHz,DMSO)δ:150.0,
148.7,141.0,132.4(CH),130.3(CH),127.6,126.0,123.7(CH),119.1(CH),116.2(CH),
114.2(CH).HR MS(ESI)m/z:328.9473[M+H]+(calcd for C12H10BrO4S+328.9478).
Embodiment 3.R1=-H, R2=-Cl, R3=-C6H5When, the system of the chloro- 2- benzenesulfonyls benzene of 3--- two amphyl of Isosorbide-5-Nitrae
It is standby
In 50mL round-bottomed flasks be added 2- chlorine 1,4-benzoquinone (0.5mmol, 71mg) and benzene sulfonic acid sodium salt (1.0mmol,
164mg), add that ammonium iodide (1.5mmol, 217mg) is adjuvant and 10mL n,N-Dimethylformamide is solvent, 30
1.5h is reacted at DEG C；After reaction, solvent is removed under reduced pressure, 10mL water is added into raffinate, two are extracted with 15mL ethyl acetate
Secondary, the brine It of extract liquor saturation is primary；Extract liquor anhydrous Na2SO4It is dry, it (is washed by column chromatography after reduced pressure
De- agent：Ethyl acetate/petroleum ether=1/5) separating-purifying, obtain yellow, viscous liquid 0.127g, yield 90.0%.
Colorless solid, mp 185-186 DEG C1H NMR(400MHz,DMSO)δ:10.26(bs,2H),7.89(d,JH-H=
7.7Hz,2H),7.67-7.63(m,1H),7.61-7.55(m,3H),6.88(s,1H).13C NMR(100MHz,DMSO)δ:
148.6,145.9,141.3,133.7(CH),129.3(CH),128.2(CH),127.1,125.7,118.8(CH),115.6
(CH).HR MS(ESI)m/z:284.9985[M+H]+(calcd for C12H10ClO4S+284.9983).
Embodiment 4.R1=-CH3, R2=-H, R3=-C6H5When, 5- methyl -2- benzenesulfonyls benzene-- two amphyl of Isosorbide-5-Nitrae
Preparation
In 50mL round-bottomed flasks be added 2- methyl-p-benzoquinones (0.5mmol, 61mg) and benzene sulfonic acid sodium salt (1.0mmol,
164mg), add that ammonium iodide (1.25mmol, 181mg) is adjuvant and 10mL dimethyl sulfoxide (DMSO)s are solvent, it is anti-at 30 DEG C
Answer 1.5h；After reaction, solvent is removed under reduced pressure, 10mL water is added into raffinate, secondary, extraction is extracted with 15mL ethyl acetate
The brine It of liquid saturation is primary；Extract liquor anhydrous Na2SO4It is dry, pass through column chromatography (eluant, eluent after reduced pressure：Second
Acetoacetic ester/petroleum ether=1/5) separating-purifying, obtain yellow, viscous liquid 0.120g, yield 91.0%.
Colorless solid, mp 154-155 DEG C1H NMR(400MHz,DMSO)δ:9.84(bs,1H),9.36(bs,1H),
7.88(d,JH-H=7.3Hz, 2H), 7.63-7.60 (m, 1H), 7.57-7.53 (m, 2H), 7.37 (s, 1H), 6.64 (s, 1H),
2.08(s,3H).13C NMR(100MHz,DMSO)δ:148.4,148.1,142.2,133.7,133.3(CH),129.2(CH),
128.0(CH),123.6,119.8(CH),113.5(CH),16.7(CH3).HR MS(ESI)m/z:265.0533[M+H]+
(calcd for C13H13O4S+265.0529).
Embodiment 5.R1=R2=-H, R3=-C2H5When, the preparation of 2- ethylsulfonyls benzene-- two amphyl of Isosorbide-5-Nitrae
1,4-benzoquinone (0.5mmol, 54mg) and ethylsulfonic acid sodium (1.0mmol, 116mg) are added in 50mL round-bottomed flasks,
It adds that ammonium iodide (2.0mmol, 290mg) is adjuvant and 10mL tetrahydrofurans are solvent, reacts 2.0h at 40 DEG C；Reaction
After, solvent is removed under reduced pressure, 10mL water is added into raffinate, it is secondary with the extraction of 15mL ethyl acetate, extract liquor saturation
Brine It is primary；Extract liquor anhydrous Na2SO4It is dry, pass through column chromatography (eluant, eluent after reduced pressure：Ethyl acetate/stone
Oily ether=1/8) separating-purifying, obtain yellow, viscous liquid 0.093g, yield 92.0%.
Colorless solid, mp 94-95 DEG C1H NMR(400MHz,DMSO)δ:8.45(bs,1H),7.82(bs,1H),7.53
(s,1H),6.95(d,JH-H=7.8Hz, 1H), 6.86 (d, JH-H=7.8Hz, 1H), 3.55 (q, JH-H=5.7Hz, 2H), 1.35
(t,JH-H=5.7Hz, 3H)13C NMR(100MHz,DMSO)δ:148.3,148.0,140.2,126.0(CH),124.3(CH),
119.4(CH),55.0(CH2),18.6(CH3).HR MS(ESI)m/z:203.0310[M+H]+(calcd for C8H11O4S+
203.0307).
Embodiment 6.R1=-H, R2=-Cl, R3=-C6H5When, the system of the chloro- 2- benzenesulfonyls naphthalenes of 3--- two amphyl of Isosorbide-5-Nitrae
It is standby
Be added in 50mL round-bottomed flasks the chloro- 1,4- naphthoquinones (0.5mmol, 96mg) of 2- and benzene sulfonic acid sodium salt (0.5mmol,
82mg), it adds that ammonium iodide (2.0mmol, 290mg) is adjuvant and 10mL methanol is solvent, reacts 1.0h at 40 DEG C；Instead
After answering, solvent is removed under reduced pressure, 10mL water is added into raffinate, secondary, extract liquor saturation is extracted with 15mL ethyl acetate
Brine It it is primary；Extract liquor anhydrous Na2SO4It is dry, pass through column chromatography (eluant, eluent after reduced pressure：Ethyl acetate/
Petroleum ether=1/10) separating-purifying, obtain yellow, viscous liquid 0.158g, yield 95.0%.
Light yellow crystal, 197-198 DEG C of fusing point；1H NMR(400MHz,DMSO)δ:10.19(bs,1H),10.03(bs,
1H),8.20(d,JH-H=8.3Hz, 1H), 8.15 (d, JH-H=8.3Hz, 1H), 7.97 (d, JH-H=7.8Hz, 2H), 7.69-
7.54(m,5H).13C NMR(100MHz,DMSO)δ:146.9,146.2,143.3,133.5(CH),129.2(CH),128.4
(CH),127.5(CH),127.0(CH),126.5,123.3(CH),122.6(CH),121.0,103.2.HR MS(ESI)m/z:
335.0142[M+H]+(calcd for C16H12ClO4S+335.0139).
Embodiment 7.R1=R2=-H, R3=-C6H5When, the preparation of 2- benzenesulfonyls naphthalene-- two amphyl of Isosorbide-5-Nitrae
1,4-naphthoquinone (0.5mmol, 79mg) and benzene sulfonic acid sodium salt (1.0mmol, 164mg) are added in 50mL round-bottomed flasks,
The mixed solvent that ammonium iodide (2.0mmol, 290mg) is adjuvant and 5mL methanol and 5mL n,N-Dimethylformamide is added,
2.0h is reacted at 40 DEG C；After reaction, solvent is removed under reduced pressure, 10mL water is added into raffinate, is extracted with 15mL ethyl acetate
Take it is secondary, extract liquor saturation brine It it is primary；Extract liquor anhydrous Na2SO4It is dry, pass through column color after reduced pressure
Compose (eluant, eluent：Ethyl acetate/petroleum ether=1/10) separating-purifying, obtain yellow, viscous liquid 0.139g, yield 93.0%.
Light yellow crystal, mp 178-179 DEG C1H NMR(400MHz,DMSO)δ:10.21(bs,1H),10.07(bs,
1H),8.17(d,JH-H=8.3Hz, 1H), 8.12 (d, JH-H=8.2Hz, 1H), 7.95 (d, JH-H=7.5Hz, 2H), 7.68-
7.56(m,5H),7.28(s,1H).13C NMR(100MHz,DMSO)δ:146.7,146.0,142.3,133.6(CH),129.5
(CH),128.8(CH),127.8(CH),127.2(CH),126.7,123.6(CH),122.8(CH),121.2,104.2(CH)
.HR MS(ESI)m/z:301.0532[M+H]+(calcd for C16H13O4S+301.0529).
Embodiment 8.R1=-OCH3,R2=-H,When, the third sulfonyl of 2- rings -7- methoxynaphthalene-Isosorbide-5-Nitrae-diphenol derives
The preparation of object
6- methoxyl group -1,4- naphthoquinones (0.5mmol, 94mg) and cyclopropyl sodium sulfonate are added in 50mL round-bottomed flasks
(1.0mmol, 128mg), adds that ammonium iodide (2.0mmol, 290mg) is adjuvant and 10mL methanol is solvent, at 40 DEG C
React 2.0h；After reaction, solvent is removed under reduced pressure, 10mL water is added into raffinate, secondary, extraction is extracted with 15mL ethyl acetate
Take the brine It that liquid is saturated primary；Extract liquor anhydrous Na2SO4It is dry, pass through column chromatography (eluant, eluent after reduced pressure：
Ethyl acetate/petroleum ether=1/10) separating-purifying, obtain yellow, viscous liquid 0.135g, yield 92.0%.
Light yellow crystal, 114-115 DEG C of fusing point；1H NMR(400MHz,CDCl3)δ:10.05(bs,1H),10.01(bs,
1H),8.53(d,JH-H=8.7Hz, 1H), 8.21 (d, JH-H=3.0Hz, 1H), 8.17 (dd, JH-H=8.7Hz, JH-H=
3.0Hz,1H),7.24(s,1H),3.94(s,3H),1.85-0.61(m,5H).13C NMR(100MHz,CDCl3)δ:160.4,
150.2,145.2,131.2,130.2,125.3(CH),122.3(CH),114.5,113.2(CH),110.6(CH),55.9,
38.4,6.5.HR MS(ESI)m/z:295.0638[M+H]+(calcd for C14H15O5S+295.0635).。
Claims (5)
1. a kind of method preparing 2- sulfonyls-- two amphyl of Isosorbide-5-Nitrae, which is characterized in that be achieved by the steps of：It will change
It closes object 1, compound 2 and ammonium iodide to be added in reactor, in organic solvent heating reaction, passes through column chromatography point after reaction
From, or carry out recrystallizing isolated 2- sulfonyls-- two amphyl of Isosorbide-5-Nitrae（I）；
In formula, R1Represent following group：Hydrogen-based, methyl, ethyl, methoxyl group or halogen；R2Represent following group：Hydrogen-based, methyl,
Ethyl, methoxyl group, ethyoxyl, nitro, amino, hydroxyl, acetoxyl group or halogen；R3Represent following group：Methyl, ethyl, ring
Propyl, phenyl, p-methylphenyl, to ethylbenzene, to tert-butyl-phenyl, p-methoxyphenyl, p-nitrophenyl, to cyano-phenyl,
To halogen phenyl or naphthyl；
The compound 1 represents benzoquinones, substitution benzoquinones or naphthoquinones, replaces naphthoquinones.
2. the preparation method of 2- sulfonyls according to claim 1-- two amphyl of Isosorbide-5-Nitrae, which is characterized in that R1It represents such as
Lower group：Hydrogen-based, methyl, ethyl or methoxyl group；R2Represent following group：Hydrogen-based, methyl, methoxyl group or halogen；R3It represents as follows
Group：Phenyl, p-methylphenyl, to tert-butyl-phenyl, p-methoxyphenyl, p-nitrophenyl, to cyano-phenyl or to halobenzene base.
3. the preparation method of 2- sulfonyls according to claim 1 or 2-- two amphyl of Isosorbide-5-Nitrae, which is characterized in that described
Solvent be dioxane, it is tetrahydrofuran, dimethyl sulfoxide, n,N-Dimethylformamide, methanol, one or more in ethyl alcohol.
4. the preparation method of 2- sulfonyls according to claim 1 or 2-- two amphyl of Isosorbide-5-Nitrae, which is characterized in that described
The molar ratio of compound 1, compound 2 and ammonium iodide is 1: 1-2 :2- 4.
5. the preparation method of 2- sulfonyls according to claim 1 or 2-- two amphyl of Isosorbide-5-Nitrae, which is characterized in that reaction
Temperature is 20-40 DEG C, and the reaction time is 0.5-2.0 hours.
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