IL39246A - The preparation of n-substituted n-chloromethyl-carbamic acid esters and thiolesters and the new thiolesters - Google Patents

The preparation of n-substituted n-chloromethyl-carbamic acid esters and thiolesters and the new thiolesters

Info

Publication number
IL39246A
IL39246A IL7239246A IL3924672A IL39246A IL 39246 A IL39246 A IL 39246A IL 7239246 A IL7239246 A IL 7239246A IL 3924672 A IL3924672 A IL 3924672A IL 39246 A IL39246 A IL 39246A
Authority
IL
Israel
Prior art keywords
carbon atoms
branched
straight
alkyl
chain
Prior art date
Application number
IL7239246A
Other versions
IL39246A0 (en
Original Assignee
Bayer Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Ag filed Critical Bayer Ag
Publication of IL39246A0 publication Critical patent/IL39246A0/en
Publication of IL39246A publication Critical patent/IL39246A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (9)

CLAIMS A process for the preparation of. an N-substituted N- 1 chloromethylcarbamic acid ester or thioleste of the general formula :- in which 1 R is alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, aryl or aralkyl, the aromatic ring of the two last- mentioned radicals optionally being substituted by. · at least one substituent selected from alkyl, halo- alkyl, alkoxy and halogen, 2 R is alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkenyl, aryl optionally carrying at least one substituent selected from alkyl, alkenyl, alkoxy, alkylthio, halogen, cycloalkyl or is aralkyl optionally being substituted in the aryl, moiety, by at least one substituent selected from alkyl, alkoxy, ■ halogen, N-chloromethyl-N-methyl-carbamoyl/anS. anellated cyclohexyl; or is the grouping and X is oxygon or sulphur in vhich an N-monoaubstituted carbaiaic acid ester or thiolester of the general formula H-N-OO-X-R2 (II) in whioh R , R and X have the meanings stated above, is reacted with paraformaldehyde and thionyl chloride, optional' ly in the presence of a diluent, at a temperature between +10°0 and +120°0. A process according to claim 1 in which R is branched or straight-chain alkyl with 1 to 20 carbon atoms, branched or straight-chain alkenyl- vith 3 to 6 carbon atoms, branched or straight-chain alkynyl with 3 to 6 carbon atoms, haloalkyl with 2 to 6 carbon atoms and
1. To 4 halogen atoms, cycloalkyl with 3 to 8 carbon atoms, aryl with 6 to 10 carbon atoms or aralkyl with 6 to 10 carbon atoms in the aryl moiety and 1 or 2 carbon atoms in the alkyl moiety, the aromatic ring of the two last-mentioned radicals optionally carrying at least one s bstituent selected from branched or straight-chain alkyl with 1 to 4 carbon atoms, branched or straight- chain alkoxy with' 1 to A carbon atoms, halogen and halo- alkyl with 1 or 2 carbon atoms and 1 to 5 fluorine or 2 chlorine atoms; and R is branched or straight-chain alkyl with 1 to 20 carbon atoms; branched or straight-chain alkenyl with 3 to 6 carbon. atoms , branched or straight- chain alkynyl with 3 to 6 carbon atoms, haloalkyl with
2. To 6 carbon atoms and 1 to 4 halogen atoms, haloalkenyl or haloalkynyl with, in either case, 3 to 6 carbon atoms and 1 to 4 halogen atoms', cycloalkyl or cycloalkenyl with, in either case, 3 to 8 carbon atoms, or aryl with 6 to 10 carbon atoms optionally being substituted by at least one substituent selected from branched or straight-chain alkyl with 1 to 4 carbon atoms, branched or straight-chain alkoxy with 1 to 4 carbon atoms , branched or straight-chain alkyl- thio with 1 to 4 carbon atoms, branched or straight-chain alkenyl with 3 to 6 carbon atoms, cycloalkyl with 5 to 7 carbon atoms and halogen; or is aralkyl with 6 to 10 carbon atoms in the aryl moiety and 1 or 2 carbon atoms in the alkyl moiety, optionally being substituted in the aryl moiety by at least one substituent selected from branched or straight- chain alkyl with 1 to 4 carbon atoms, branched or straight- chain alkoxy with 1 to 4 <¾^bo atoms, halogen, N-chloro- methyl-N-methyl-carbamoy and anellated oyclohexyl; or is the grouping -32- 39246/2
3. A process according to claim 1 or 2 in which the reaction is effected in the presence of an inert solvent.
4. A process according to claim 3 in which the solvent is benzene or toluene.
5. -A process according to any of claims 1 to 4 in which the reaction is effected at between +15°C and +70°C.
6. A process according to any of claims 1 to 5 in which the -monosubstituted carbamic acid ester or thiolester (II), paraformaldehyde and thionyl chloride are used in substantially equimolar amounts.
7. A process according to any of claims 1 to 6 in which the 13-monosubstituted carbamic acid ester or thiolester (II) is one that is hereinbefore specifically mentioned.
8. A process for the preparation of an N-substituted K-chloromethylcarbamic acid ester or thiolester of the formula (I) substantially as hereinbefore described in any of Examples 1 to 169. 9. A process for the preparation of an K-substituted -chloro ethylcarbamic acid ester or thiolester of the formula (I) substantially as hereinbefore described in any of Examples 170 to 191. 10. F-substituted H-chloromethylcarbamic acid esters and thiolesters whenever prepared by a process according to any of claims 1 to 8. 11. K-substituted N-chloromethylcarbamic acid esters and thiolesters whenever prepared by a process according to claim
9. 39246/3 - 33 - 12) The tJ-Aryl-B-chlormethylesrbaniic acid thiolesters of the general formula ClCH -K-C0-S-R ^ 1t (III) in which R represents phenyl, optionally substituted by one or more halogen atoms, and represents straight-chain or branched alkyl with 1 to 4 carbon atoms. HE:PE
IL7239246A 1971-04-22 1972-04-18 The preparation of n-substituted n-chloromethyl-carbamic acid esters and thiolesters and the new thiolesters IL39246A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19712119518 DE2119518A1 (en) 1971-04-22 1971-04-22 Process for the preparation of N-substituted N-chloromethyl carbamic acid esters and thiol esters

Publications (2)

Publication Number Publication Date
IL39246A0 IL39246A0 (en) 1972-06-28
IL39246A true IL39246A (en) 1976-01-30

Family

ID=5805461

Family Applications (1)

Application Number Title Priority Date Filing Date
IL7239246A IL39246A (en) 1971-04-22 1972-04-18 The preparation of n-substituted n-chloromethyl-carbamic acid esters and thiolesters and the new thiolesters

Country Status (13)

Country Link
AT (1) AT317242B (en)
BE (1) BE782383A (en)
CH (1) CH566971A5 (en)
DD (1) DD98513A5 (en)
DE (1) DE2119518A1 (en)
FR (1) FR2136602A5 (en)
GB (1) GB1350528A (en)
HU (1) HU164706B (en)
IL (1) IL39246A (en)
IT (1) IT957202B (en)
NL (1) NL7205271A (en)
PL (1) PL83653B1 (en)
SU (1) SU443510A3 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2854599A1 (en) 1978-12-18 1980-06-26 Basf Ag SUBSTITUTED N-HALOGEN METHYLANILIDES AND METHOD FOR THE PRODUCTION AND USE THEREOF
DE4237617A1 (en) * 1992-11-06 1994-05-11 Bayer Ag Use of substituted benzimidazoles
DE19642529A1 (en) 1996-10-15 1998-04-16 Bayer Ag Aminophenol derivatives
DE19831985A1 (en) 1998-07-16 2000-01-20 Bayer Ag New tetrafluoroethylenedioxy-benzimidazole derivatives useful as antiparasitic agents, especially for treating coccidiosis in poultry
TWI730297B (en) * 2018-02-27 2021-06-11 日商組合化學工業股份有限公司 Method for manufacturing mercaptophenol compound and intermediate thereof

Also Published As

Publication number Publication date
BE782383A (en) 1972-10-20
NL7205271A (en) 1972-10-24
DD98513A5 (en) 1973-06-20
HU164706B (en) 1974-04-11
CH566971A5 (en) 1975-09-30
IT957202B (en) 1973-10-10
GB1350528A (en) 1974-04-18
AT317242B (en) 1974-08-26
SU443510A3 (en) 1974-09-15
IL39246A0 (en) 1972-06-28
FR2136602A5 (en) 1972-12-22
PL83653B1 (en) 1975-12-31
DE2119518A1 (en) 1972-10-26

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