JPH0140818B2 - - Google Patents
Info
- Publication number
- JPH0140818B2 JPH0140818B2 JP56087127A JP8712781A JPH0140818B2 JP H0140818 B2 JPH0140818 B2 JP H0140818B2 JP 56087127 A JP56087127 A JP 56087127A JP 8712781 A JP8712781 A JP 8712781A JP H0140818 B2 JPH0140818 B2 JP H0140818B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- bromo
- formula
- solution
- general formula
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 239000007864 aqueous solution Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 14
- 239000003513 alkali Substances 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 29
- -1 carboxylic acid halides Chemical class 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 235000011121 sodium hydroxide Nutrition 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- DSJWOLVWBVIHRB-UHFFFAOYSA-N 2-bromo-3,3-dimethylbutanoyl chloride Chemical compound CC(C)(C)C(Br)C(Cl)=O DSJWOLVWBVIHRB-UHFFFAOYSA-N 0.000 description 8
- KDFDOINBXBEOLZ-UHFFFAOYSA-N 2-phenylpropan-2-amine Chemical compound CC(C)(N)C1=CC=CC=C1 KDFDOINBXBEOLZ-UHFFFAOYSA-N 0.000 description 8
- 150000003939 benzylamines Chemical class 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- WINUYYILZBTJTR-UHFFFAOYSA-N 2-bromo-3,3-dimethylbutanoyl bromide Chemical compound CC(C)(C)C(Br)C(Br)=O WINUYYILZBTJTR-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- BUTKIHRNYUEGKB-UHFFFAOYSA-N 3,3-dimethylbutanoyl chloride Chemical compound CC(C)(C)CC(Cl)=O BUTKIHRNYUEGKB-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 238000007112 amidation reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- IIJNPKVOYPDSMV-UHFFFAOYSA-N 2-bromo-3,3-dimethyl-n-(1-phenylethyl)butanamide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)C1=CC=CC=C1 IIJNPKVOYPDSMV-UHFFFAOYSA-N 0.000 description 1
- YXYHDYAMHIWFKK-UHFFFAOYSA-N 2-chloro-3,3-dimethylbutanoyl chloride Chemical compound CC(C)(C)C(Cl)C(Cl)=O YXYHDYAMHIWFKK-UHFFFAOYSA-N 0.000 description 1
- KLSHSRMTFOMARP-UHFFFAOYSA-N 2-ethyl-3,3-dimethylbutanoyl chloride Chemical compound CCC(C(Cl)=O)C(C)(C)C KLSHSRMTFOMARP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 239000011356 non-aqueous organic solvent Substances 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8712781A JPS57203049A (en) | 1981-06-05 | 1981-06-05 | Preparation of amide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8712781A JPS57203049A (en) | 1981-06-05 | 1981-06-05 | Preparation of amide derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57203049A JPS57203049A (en) | 1982-12-13 |
| JPH0140818B2 true JPH0140818B2 (US20070167544A1-20070719-C00007.png) | 1989-08-31 |
Family
ID=13906288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8712781A Granted JPS57203049A (en) | 1981-06-05 | 1981-06-05 | Preparation of amide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57203049A (US20070167544A1-20070719-C00007.png) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5810545A (ja) * | 1981-07-10 | 1983-01-21 | Sumitomo Chem Co Ltd | Ｎ−メチルベンジル−ハロアセタミド誘導体、その製造法およびこれらを有効成分として含有する農園芸用殺菌剤 |
| JPS5813554A (ja) * | 1981-07-14 | 1983-01-26 | Sumitomo Chem Co Ltd | Ｎ―メチルベンジル―ハロアセタミド誘導体を有効成分として含有する農園芸用殺菌剤 |
| JPS5829751A (ja) * | 1981-08-12 | 1983-02-22 | Sumitomo Chem Co Ltd | Ｎ―ベンジル―ハロアセタミド誘導体を有効成分として含有する農園芸用殺菌剤 |
| JPS5829752A (ja) * | 1981-08-13 | 1983-02-22 | Sumitomo Chem Co Ltd | 光学活性ｎ−ベンジル−ハロアセタミド誘導体、その製造法およびこれらを有効成分として含有する農園芸用殺菌剤 |
| KR20160074540A (ko) * | 2013-10-17 | 2016-06-28 | 다우 아그로사이언시즈 엘엘씨 | 살충성 화합물의 제조 방법 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56104854A (en) * | 1980-01-23 | 1981-08-20 | Sumitomo Chem Co Ltd | N-dimethylbenzyl-t-butylacetamide derivative, its preparation, and herbicide containing said compound as effective component |
| JPS56123957A (en) * | 1980-03-04 | 1981-09-29 | Sumitomo Chem Co Ltd | N-dimethylbenzyl-tert-butylacetamide derivative, its preparation and herbicide containing the same as active constituent |
| JPS57188552A (en) * | 1981-05-12 | 1982-11-19 | Sumitomo Chem Co Ltd | Tert-butylacetamide derivative, its preparation, and agricultural and horticultural fungicide containing said derivative as active component |
-
1981
- 1981-06-05 JP JP8712781A patent/JPS57203049A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56104854A (en) * | 1980-01-23 | 1981-08-20 | Sumitomo Chem Co Ltd | N-dimethylbenzyl-t-butylacetamide derivative, its preparation, and herbicide containing said compound as effective component |
| JPS56123957A (en) * | 1980-03-04 | 1981-09-29 | Sumitomo Chem Co Ltd | N-dimethylbenzyl-tert-butylacetamide derivative, its preparation and herbicide containing the same as active constituent |
| JPS57188552A (en) * | 1981-05-12 | 1982-11-19 | Sumitomo Chem Co Ltd | Tert-butylacetamide derivative, its preparation, and agricultural and horticultural fungicide containing said derivative as active component |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57203049A (en) | 1982-12-13 |
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