Triethylamine → Methanesulfonic acid 5-(3-chloro-4-cyano-phenoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethyl ester

HRID 2233592Notes

Reaction equation

HRID 2233592 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[S:16][C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[N:14][C:13]=2[CH2:27][OH:28])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:9]=[C:8]([CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[O:10][CH2:11][C:12]1[S:16][C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:24])[F:26])=[CH:19][CH:18]=2)=[N:14][C:13]=1[CH2:27][O:28][S:30]([CH3:29])(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 592961782-Chloro-4-[4-hydroxymethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile

Product 1

HCID 59296164Methanesulfonic acid 5-(3-chloro-4-cyano-phenoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.8 g 2-Chloro-4-[4-hydroxymethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile were suspended in 50 ml dichloromethane and cooled in an ice bath. 0.39 ml methanesulfonylchloride and 0.89 ml triethylamine were added. The resulting mixture was stirred at 0° C. for one hour then washed with water and brine, dried over MgSO4. The solvent was removed in vacuo to obtain 1.0 g methanesulfonic acid 5-(3-chloro-4-cyano-phenoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethyl ester as pale yellow solid.

Workup

  1. temperaturecooled in an ice bath
  2. washthen washed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-93fdfd7424f44c0b935b3a1c79aba53f
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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