Dichloromethane → 6,6-Difluoro-5-methyl-5-hexenyl benzothiazole-2-carboxylate

HRID 917365

反応式

HRID 917365 の反応式
ClCCl.[S:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[C:13]([OH:15])=[O:14].[F:16][C:17]([F:25])=[C:18]([CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22]O.CN(C1C=CC=CN=1)C>O>[S:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[C:13]([O:15][CH2:22][CH2:21][CH2:20][CH2:19][C:18]([CH3:24])=[C:17]([F:25])[F:16])=[O:14]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 218852-DimethylaminopyridineHCID 5850531,3-Benzothiazole-2-carboxylic acidHCID 230201726,6-Difluoro-5-methyl-5-hexenol

生成物 1

HCID 230202126,6-Difluoro-5-methyl-5-hexenyl benzothiazole-2-carboxylate収率 43.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To 4 ml of dichloromethane were dissolved 0.24 g (1.3 mmol) of benzothiazole-2-carboxylic acid, manufactured by a method described in “J. Amer. Chem. Soc.”, page 2328 (1949), 0.17 g (1.1 mmol) of 6,6-difluoro-5-methyl-5-hexenol and 0.13 g (1.1 mmol) of dimethylaminopyridine, followed by the addition of 0.38 g (2.0 mmol) of N-ethyl-N′-3-dimethyl-aminopropylcarbodiimide (WSC) hydrochloric acid salt at room temperature and stirring at the same temperature for 20 hours. The reaction liquid was then poured in water and extracted with dichloromethane. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:6) to obtain 0.15 g (yield: 43%) of 6,6-difluoro-5-methyl-5-hexenyl benzothiazole-2-carboxylate.

後処理

  1. customThe reaction liquid
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:6)

出典と根拠

ORDレコード
ord-5fb6932d18f94b5abc7ceab892efd65f
出典データセット
uspto-grants-2007_09
特許番号
US07273878B2

関連ノート

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