Triethylamine → 2-(3-Chloroprop-1-en-1-yl)-4-(4-fluorophenyl)-1,3-thiazole

HRID 238295Notes

Reaction equation

HRID 238295 reaction equation
CS([Cl:5])(=O)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([CH:18]=[CH:19][CH2:20]O)[S:16][CH:17]=2)=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[Cl:5][CH2:20][CH:19]=[CH:18][C:15]1[S:16][CH:17]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=2)[N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 688230923-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]prop-2-en-1-ol

Product 1

HCID 688217062-(3-Chloroprop-1-en-1-yl)-4-(4-fluorophenyl)-1,3-thiazoleYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

258 μl (3.3 mmol) of methanesulfonyl chloride were slowly added to 265 mg (1.12 mmol) of 3-(4-(4-fluorophenyl)thiazol-2-yl)prop-2-en-1-ol and 456 mg (4.5 mmol) of triethylamine in 10 ml of dichloromethane at room temperature and the mixture was stirred for 3 h. After standing at room temperature over the weekend, the mixture was extracted with a sodium hydrogencarbonate solution. Evaporation of the organic phase yielded 280 mg of the title compound.

Workup

  1. customAfter standing at room temperature over the weekend
  2. extractionthe mixture was extracted with a sodium hydrogencarbonate solution
  3. customEvaporation of the organic phase

Sources & evidence

ORD record
ord-3d3a641aff964950bcef4a0f10057b06
Source dataset
uspto-grants-2014_02
Patent number
US08642620B2

Reaction notes

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