Dimethylformamide → HCID 86713745, compound

HRID 2274003Notes

Reaction equation

HRID 2274003 reaction equation
[Cl:1][C:2]1C=[CH:9][C:8]([N:11]([CH3:28])[C:12]([C:14]2[N:18]([CH3:19])[N:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[C:15]=2[C:24]([F:27])([F:26])[F:25])=[O:13])=[CH:7][C:3]=1C(O)=O.CN(C)C=O.[C:34](Cl)(=O)[C:35]([Cl:37])=[O:36]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:7][C:8]([N:11]([CH3:28])[C:12]([C:14]2[N:18]([CH3:19])[N:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[C:15]=2[C:24]([F:25])([F:26])[F:27])=[O:13])=[CH:9][C:34]=1[C:35]([Cl:37])=[O:36]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 86713746HCID 86713746, compound

Product 1

HCID 86713745HCID 86713745, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150.0 mg (0.29 mmol) of 2-chloro-5-(methyl{[1-methyl-3,4-bis(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzoic acid are suspended in 5.0 ml of dichlormethane p.a. 0.02 ml of N,N-dimethylformamide p.a. and 0.075 ml (0.86 mmol) oxalyl chloride are then added successively to the suspension. The reaction mixture is stirred at room temperature for 0.5 h and then heated under reflux for 40 minutes. The solvent is removed under reduced pressure on a rotary evaporator. The 2-chloro-5-(methyl{[1-methyl-3,4-bis(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl chloride formed is used for the subsequent synthesis step without further purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 40 minutes
  3. customThe solvent is removed under reduced pressure on a rotary evaporator

Sources & evidence

ORD record
ord-7b9e4046ebdf4305900184bf37dffbcc
Source dataset
uspto-grants-2015_09
Patent number
US09126945B2

Reaction notes

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