Thionyl Chloride → HCID 178461992, compound

HRID 46144Notes

Reaction equation

HRID 46144 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[S:12][C:13]([C:18]3[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=3)([CH3:17])[C:14](=[O:16])[N:15]=2)[CH3:9])=[CH:4][CH:3]=1.S(Cl)([Cl:29])=O>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[S:12][C:13]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([Cl:29])=[O:23])=[CH:20][CH:19]=3)([CH3:17])[C:14](=[O:16])[N:15]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 178461994HCID 178461994, compound

Product 1

HCID 178461992HCID 178461992, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-((S)-1-(4-fluorophenyl)ethylamino)-5-methyl-4-oxo-4,5-dihydrothiazol-5-yl)benzoic acid (0.48 g, 1.29 mmol) in CH2Cl2 (6 mL) was added thionyl chloride (Aldrich, 0.19 ml, 2.58 mmol), and 2 drops of DMF. After stirring the mixture overnight at ambient temp., the crude product was concentrated in vacuo and dried on high vacuum. The product was used in next step without purification.

Workup

  1. concentrationthe crude product was concentrated in vacuo
  2. customdried on high vacuum
  3. customThe product was used in next step without purification

Sources & evidence

ORD record
ord-5d5220e54b2d47a5a6db62901d646745
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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