Triethylamine → Thiazole, 5-(chloromethyl)-2-[4-(trifluoromethyl)phenyl]-

HRID 1393077노트

반응식

HRID 1393077 반응식
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([CH2:14]O)=[CH:12][N:13]=2)=[CH:5][CH:4]=1.CCN(CC)CC.CS([Cl:29])(=O)=O.CCCCCCC.CCOC(C)=O>C(Cl)Cl>[Cl:29][CH2:14][C:11]1[S:10][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=2)=[N:13][CH:12]=1

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 31297Methanesulfonyl chloride2회HCID 21899848Ethylacetate heptaneHCID 22647407{2-[4-(Trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanol

생성물 1

HCID 22647608Thiazole, 5-(chloromethyl)-2-[4-(trifluoromethyl)phenyl]-수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To an ice-cooled solution of [2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol (1.556 g, 6.0 mmol) and Et3N (1.67 ml, 12.0 mmol) in CH2Cl2 (14 ml) was slowly added methanesulfonyl chloride (0.75 ml, 9.6 mmol). After 2 h at 0° C. more Et3N (0.17 ml, 1.2 mmol) and methanesulfonyl chloride (0.07 ml, 0.96 mmol) were added. The reaction was kept for 16 h at 0° C. and 4 h at RT until the reaction was completed by TLC (n-heptane/EtOAc 4:1). The reaction was then partitioned between Et2O (3×)/aqueous saturated NaHCO3. The organic phases were washed once with aqueous 10% KHSO4. and aqueous 10% NaCl, dried over Na2SO4 and evaporated to give 1.58 g (95%) of 5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole as a light yellow solid, MS: 277 (M, 1Cl), MP: 55-57° C.

후처리

  1. customThe reaction was then partitioned between Et2O (3×)/aqueous saturated NaHCO3
  2. washThe organic phases were washed once with aqueous 10% KHSO4
  3. dry with materialand aqueous 10% NaCl, dried over Na2SO4
  4. customevaporated

출처 및 근거

ORD 기록
ord-3c2e08c709054213a82909bb8a45fd19
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07345067B2

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