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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
ノート
印刷プレビュー

反応式

HRID 399634 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049
Pyridine
溶媒
HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c3abf37985a04eedbdaced9381a9dde5
出典データセット
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05821255

反応ノート

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