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Thionyl Chloride → 5-(Chloromethyl)-4-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazole

HRID 1767927
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반응식

HRID 1767927 반응식
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[S:5][C:6]=1[CH2:7]O.S(Cl)([Cl:21])=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:21][CH2:7][C:6]1[S:5][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[N:3][C:2]=1[CH3:1]
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참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 22647518{4-Methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanol

생성물 1

HCID 236145055-(Chloromethyl)-4-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazole수율 94%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of [4-methyl-2-(3-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol (1.2 g, 4.4 mmol) in chloroform (7 ml) was added thionyl chloride (0.64 ml, 8.8 mmol) at −10° C. under an argon atmosphere. The reaction mixture was stirred for 30 min, saturated aqueous sodium bicarbonate solution/ice water 1/1 was added and the layers were separated. The aqueous layer was extracted two times with dichloromethane. The combined organic layers were washed with ice water/brine 1/1 and dried over sodium sulfate. The solvent was evaporated in vacuo to give the title compound (1.2 g, 4.1 mmol, 94%) as yellow oil which was used in the next step without further purification.

후처리

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted two times with dichloromethane
  3. washThe combined organic layers were washed with ice water/brine 1/1
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-11107a143e3c47f78b44c83d7bf19a2b
출처 데이터셋
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07235572B2

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