Dimethylformamide → 2-(4-Chlorophenoxy)benzeneacetyl chloride

HRID 2421575노트

반응식

HRID 2421575 반응식
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][C:14](O)=[O:15])=[CH:4][CH:3]=1.CN(C)C=O.O=S(Cl)[Cl:26]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][C:14]([Cl:26])=[O:15])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 122458712-(2-(4-Chlorophenoxy)phenyl)acetic acid

생성물 1

HCID 231486612-(4-Chlorophenoxy)benzeneacetyl chloride

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

[2-(4-chloro-phenoxy)-phenyl]-acetic acid (IX) (47.3 grams; 180 mmol) was suspended in toluene (140 ml) at 48° C. To this suspension dimethylformamide (4.0 ml) and SOCl2 (19.8 ml; 271 mmol; 1.5 eq) in toluene (18 ml) were added. After 10 min the reaction mixture was concentrated under vacuo and stripped twice with toluene, to yield a brownish oil of [2-(4-chlorophenoxy)-phenyl]-acetyl chloride. The oil was suspended in toluene (75 ml). To the suspension was added at 5° C. a solution of sarcosine methylester (30.3 grams 217 mmol) and triethylamine (57 ml) in a mixture of dimethylformamide (236 ml) and toluene (47 ml). The brownish suspension was stirred for 2 hours at room temperature. To the reaction mixture water (750 ml) was added and the mixture was extracted twice with ethyl acetate (500 ml). The organic phase was washed with saturated brine (700 ml) and dried on magnesium sulphate. The solvent was removed in vacuum to yield methyl-N-[2-(4-chloro-2-phenoxyphenyl)-1-oxethyl]-N-methylglycinate (X) (61.3 grams, 202 mmol) as a brownish oil.

후처리

  1. concentrationAfter 10 min the reaction mixture was concentrated under vacuo

출처 및 근거

ORD 기록
ord-4bc9c513c29840c694311a8ad432d778
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956202B2

반응 노트

불러오는 중…