Thionyl Chloride → HCID 23614504, compound

HRID 1767972Notes

Reaction equation

HRID 1767972 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[C:13]1[S:14][C:15]([CH2:19]O)=[C:16]([CH3:18])[N:17]=1.S(Cl)([Cl:23])=O.C(=O)(O)[O-].[Na+].Cl.O>C(Cl)(Cl)Cl>[Cl:23][CH2:19][C:15]1[S:14][C:13]([C:3]2[CH:4]=[CH:5][C:6]([C:9]([F:12])([F:11])[F:10])=[C:7]([F:8])[C:2]=2[F:1])=[N:17][C:16]=1[CH3:18]

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 21885828Hydrate;hydrochlorideHCID 23614483{2-[2,3-Difluoro-4-(trifluoromethyl)phenyl]-4-methyl-1,3-thiazol-5-yl}methanol

Product 1

HCID 23614504HCID 23614504, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of [2-(2,3-difluoro-4-trifluoromethyl-phenyl)-4-methyl-thiazol-5-yl]-methanol (45 mg, 150 μmol) in chloroform (3 ml) was added thionyl chloride (20 μl, 290 μmol) at −10° C. under an argon atmosphere. The reaction mixture was stirred for 30 min, saturated aqueous sodium bicarbonate solution/ice water 1/1 was added and the layers were separated. The aqueous layer was extracted two times with dichloromethane. The combined organic layers were washed with ice water/brine 1/1 and dried over sodium sulfate. The solvent was evaporated in vacuo to give the title compound (44 mg, 134 μmol, 90%) as yellow oil which was used in the next step without further purification.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted two times with dichloromethane
  3. washThe combined organic layers were washed with ice water/brine 1/1
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-104784d10e4c40748b87108e7decb2b3
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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