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

HRID 917365Notes

Reaction equation

HRID 917365 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5fb6932d18f94b5abc7ceab892efd65f
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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