Dimethylformamide → 2-Chloro-4-(2'-methylpropionamido)benzoyl chloride

HRID 359052Notes

Reaction equation

HRID 359052 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Cl:7][C:8]1[CH:16]=[C:15]([NH:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH:14]=[CH:13]C=1C(O)=O.CN(C=O)C>C1COCC1.CN(C=O)C>[Cl:7][C:8]1[CH:16]=[C:15]([NH:17][C:18](=[O:22])[CH:19]([CH3:20])[CH3:21])[CH:14]=[CH:13][C:1]=1[C:2]([Cl:4])=[O:3]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 216426412-Chloro-4-(isobutyrylamino)benzoic acid

Product 1

HCID 216426352-Chloro-4-(2'-methylpropionamido)benzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Oxalyl chloride (0.63 g) in dry THF (5 ml) was added dropwise over 5 minutes to a solution of 2-chloro-4-(2'-methylpropionamido)benzoic acid (1.0 g) in dry THF (5 ml) at room temperature. After completion of the addition, dry DMF (1 drop) was added causing vigorous effervescence and a slight temperature rise. After stirring for 4 hours and addition of a further drop of DMF, the THF was evaporated to yield 2-chloro-4-(2'-methylpropionamido)benzoyl chloride as a viscous brown gum which was used without further purification. IR (liquid film): 3320, 3260, 3160, 3070, 1780, 1710, 1680, cm-1.

Workup

  1. additionwas added
  2. customthe THF was evaporated

Sources & evidence

ORD record
ord-58c21adced9641d1a5982b8391521cd7
Source dataset
uspto-grants-1991_03
Patent number
US04999381

Reaction notes

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