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

HRID 2201894Notes

Reaction equation

HRID 2201894 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]([OH:16])=O)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.CN(C=O)C.C(Cl)(=O)C([Cl:25])=O>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]([Cl:25])=[O:16])[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 210815301-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
14.5 °C

Procedure

A reactor was charged with 1-(4-fluoro-phenylcarbamoyl)-cyclopropanecarboxylic acid (35 kg), 344 g DMF, and 175 kg THF. The reaction mixture was adjusted to 12 to 17° C. and then to the reaction mixture was charged 19.9 kg of oxalyl chloride over a period of 1 hour. The reaction mixture was left stirring at 12 to 17° C. for 3 to 8 hours. This solution was used in the next step without further processing.

Workup

  1. customwas adjusted to 12 to 17° C.
  2. waitThe reaction mixture was left

Sources & evidence

ORD record
ord-0c6e72a1a5db41a88edaf713ea264b61
Source dataset
uspto-grants-2016_06
Patent number
US09365516B2

Reaction notes

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