Triethylamine → HCID 21300959, compound

HRID 490703Notes

Reaction equation

HRID 490703 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([C:13]2[S:14][C:15]([CH2:19]O)=[C:16]([CH3:18])[N:17]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N(CC)CC)C.CS([Cl:34])(=O)=O>ClCCl>[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([C:13]2[S:14][C:15]([CH2:19][Cl:34])=[C:16]([CH3:18])[N:17]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21300958HCID 21300958, compound

Product 1

HCID 21300959HCID 21300959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

[2-(3,5-Bis-trifluoromethyl-phenyl)-4-methyl-thiazol-5-yl]-methanol (0.460 g, 1.35 mmol), is dissolved in anhydrous dichloromethane (6 mL) and cooled to 0° C. with stirring under nitrogen. Triethyl amine (0.350 mL, 2.60 mmol) and methane sulfonyl chloride (0.200 mL, 2.0 mmol) are added and the reaction is monitored by TLC. After the starting material is completely consumed, the reaction is diluted with dichloromethane and extracted against saturated sodium bicarbonate solution. The two phases are separated and the organic layer is washed with water and brine, dried over sodium sulfate, then concentrated. The residue is further purified using flash column chromatography. The 2-(3,5-Bis-trifluoromethyl-phenyl)-5-chloromethyl-4-methyl-thiazole is formed quantitatively and used without further purification.

Workup

  1. customAfter the starting material is completely consumed
  2. additionthe reaction is diluted with dichloromethane
  3. extractionextracted against saturated sodium bicarbonate solution
  4. customThe two phases are separated
  5. washthe organic layer is washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is further purified

Sources & evidence

ORD record
ord-8d6a18f39b604bfaa509f092ec89091e
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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