p-Toluenesulfonic acid monohydrate → 2-Chloro-4-[4-hydroxymethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile

HRID 2233591Notes

Reaction equation

HRID 2233591 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][O:28]C2CCCCO2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[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:24])([F:26])[F:25])=[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]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 592961302-Chloro-4-[4-(tetrahydro-pyran-2-yloxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile

Product 1

HCID 592961782-Chloro-4-[4-hydroxymethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrileYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.1 g 2-Chloro-4-[4-(tetrahydro-pyran-2-yloxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile were dissolved in 50 ml methanol. 320 mg p-toluenesulfonic acid monohydrate were added and the mixture was stirred for one hour at room temperature. The solvent was removed in vacuo and the residue was dissolved in ethylacetate and washed twice with saturated NaHCO3 solution and brine then dried over MgSO4. The solvent was removed in vacuo to obtain 3.4 g 2-Chloro-4-[4-hydroxymethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile as pale yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethylacetate
  3. washwashed twice with saturated NaHCO3 solution and brine
  4. dry with materialthen dried over MgSO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-06c4d29afca744658d17a7fb303489e7
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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