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

HRID 1767927
ノート
印刷プレビュー

反応式

HRID 1767927 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-11107a143e3c47f78b44c83d7bf19a2b
出典データセット
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07235572B2

反応ノート

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