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Methanol → 4-(2,4-dichlorophenyl)-5-methyl-2-{N-{alpha-cyclopropyl-4-[3-(chloromethyl)benzoyloxymethyl]benzyl}-N-propylamino}thiazole

HRID 399634
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HRID 399634 반응식
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1[N:21]=[C:22]([N:26]([CH:30]([CH:39]2[CH2:41][CH2:40]2)[C:31]2[CH:36]=[CH:35][C:34]([CH2:37][OH:38])=[CH:33][CH:32]=2)[CH2:27][CH2:28][CH3:29])[S:23][C:24]=1[CH3:25].CO>N1C=CC=CC=1.C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1[N:21]=[C:22]([N:26]([CH:30]([CH:39]2[CH2:40][CH2:41]2)[C:31]2[CH:32]=[CH:33][C:34]([CH2:37][O:38][C:6](=[O:7])[C:5]3[CH:9]=[CH:10][CH:11]=[C:3]([CH2:2][Cl:1])[CH:4]=3)=[CH:35][CH:36]=2)[CH2:27][CH2:28][CH3:29])[S:23][C:24]=1[CH3:25]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 887MethanolHCID 27333243-(Chloromethyl)benzoyl chlorideHCID 152916114-(2,4-dichlorophenyl)-5-methyl-2-{N-[alpha-cyclopropyl-4-(hydroxymethyl)benzyl]N-propylamino}thiazole

생성물 1

HCID 189678354-(2,4-dichlorophenyl)-5-methyl-2-{N-{alpha-cyclopropyl-4-[3-(chloromethyl)benzoyloxymethyl]benzyl}-N-propylamino}thiazole수율 81%

시약·촉매·용매 2

HCID 1049
Pyridine
용매
HCID 6344Dichloromethane용매

실험 절차

0.6 ml of 3-chloromethylbenzoyl chloride is added dropwise, at 0° C., to 1.6 g of the compound of Example 4 dissolved in 10 ml of anhydrous pyridine. After 2 hours at 0° C., methanol is added to hydrolyze the excess acid chloride and the organic phase is diluted with methylene chloride. This is then washed with 2N hydrochloric acid, with saturated aqueous sodium bicarbonate and then with saturated aqueous sodium chloride and dried over anhydrous sodium sulphate. The organic solvent is evaporated off and the product is purified on a column of silica, using a mixture of cyclohexane and ethyl acetate (20:1 v/v) as eluent, to give the expected product.

후처리

  1. washThis is then washed with 2N hydrochloric acid, with saturated aqueous sodium bicarbonate
  2. dry with materialwith saturated aqueous sodium chloride and dried over anhydrous sodium sulphate
  3. customThe organic solvent is evaporated off
  4. customthe product is purified on a column of silica
  5. additiona mixture of cyclohexane and ethyl acetate (20:1 v/v) as eluent

출처 및 근거

ORD 기록
ord-c3abf37985a04eedbdaced9381a9dde5
출처 데이터셋
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05821255

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