Thionyl Chloride → 5-(1-Chloroethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole

HRID 1767909Notes

Reaction equation

HRID 1767909 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[S:5][C:6]=1[C@H:7](O)[CH3:8].S(Cl)([Cl:22])=O>ClCCl>[Cl:22][CH:7]([C:6]1[S:5][C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:3][C:2]=1[CH3:1])[CH3:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58697769HCID 58697769, compound

Product 1

HCID 236145145-(1-Chloroethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [rac]-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanol (200 mg, 0.7 mmol; PCT Int. Appl. (2002), WO 02/062774 A1) in dichloromethane (2 ml) was added thionyl chloride (0.1 ml, 1.4 mmol) at −10° C. The cooling bath was removed after 10 min and stirring was continued for 30 min. The solvent was removed under reduced pressure and the residue dried under vacuo to give 220 mg (0.7 mmol, quant.) of the title compound as yellow solid which was used in the next step without further purification.

Workup

  1. customThe cooling bath was removed after 10 min
  2. customThe solvent was removed under reduced pressure
  3. customthe residue dried under vacuo

Sources & evidence

ORD record
ord-2726543368f7454295814a4676bdc3bd
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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