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

HRID 2201893Notes

Reaction equation

HRID 2201893 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.CN(C)C=O>[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

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (12.6 kg) was added to a solution of 1-(4-fluoro-phenylcarbamoyl)-cyclopropanecarboxylic acid (22.8 kg) in a mixture of THF (96.1 kg) and N,N-dimethylformamide (DMF; 0.23 kg) at a rate such that the batch temperature did not exceed 25° C. This solution was used in the next step without further processing.

Workup

  1. customdid not exceed 25° C

Sources & evidence

ORD record
ord-6020a6cc2ba9416d8aa1cad6620bc421
Source dataset
uspto-grants-2016_06
Patent number
US09365516B2

Reaction notes

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