Oxalyl chloride → 1-[(4-Fluorophenyl)carbamoyl]cyclopropanecarbonyl chloride

HRID 2201897Notes

Reaction equation

HRID 2201897 reaction equation
C(Cl)(=O)C([Cl:4])=O.[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2([C:20]([OH:22])=O)[CH2:19][CH2:18]2)=[O:16])=[CH:10][CH:9]=1>C1COCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2([C:20]([Cl:4])=[O:22])[CH2:19][CH2:18]2)=[O:16])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 210815301-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid

Product 1

HCID 580832671-[(4-Fluorophenyl)carbamoyl]cyclopropanecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (291 mL) was added slowly to a cooled (approximately 5° C.) solution of 1-(4-fluoro-phenylcarbamoyl)-cyclopropanecarboxylic acid in THF at a rate such that the batch temperature did not exceed 10° C. When the addition was complete, the batch was allowed to warm to ambient temperature and held with stirring for approximately 2 hours, at which time in process HPLC analysis indicated the reaction was complete. The solution was used in the next step without further processing.

Workup

  1. customdid not exceed 10° C
  2. additionWhen the addition

Sources & evidence

ORD record
ord-430ed98523614c4ba5f8c748237175d0
Source dataset
uspto-grants-2016_06
Patent number
US09365516B2

Reaction notes

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