Dimethylamine, hydrochloride → 2-chloro-N,N-dimethyl-4-nitrobenzamide

HRID 1442643Notes

Reaction equation

HRID 1442643 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].Cl.[CH3:15][NH:16][CH3:17]>C1COCC1.Cl>[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([N:16]([CH3:17])[CH3:15])=[O:5]

Participants

5

Reactant 2

HCID 10473Dimethylamine, hydrochlorideHCID 81522Benzoyl chloride, 2-chloro-4-nitro-

Product 1

HCID 32645532-chloro-N,N-dimethyl-4-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-chloro-4-nitrobenzoyl chloride Compound 13a1 (7.08 g, 32.2 mmol) and dimethylamine hydrochloride (2.62 g, 32.2 mmol) were combined in THF (50 mL) at 0° C. TEA (8.97 mL, 64.4 mmol) was added and the mixture was heated at reflux for 18 hrs. When the reaction was complete, the mixture was diluted with 1N HCl and extracted with EtOAc. The product was isolated by flash chromatography (30-50% EtOAc/hexane gradient) to provide 2-chloro-N,N-dimethyl-4-nitro-benzamide Compound 13a2 (3.05 g) as a tan solid. MS 229 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 hrs
  3. extractionextracted with EtOAc
  4. customThe product was isolated by flash chromatography (30-50% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-6fd098a910c04dc3a2df9164f9949f82
Source dataset
uspto-grants-2010_02
Patent number
US07659284B2

Reaction notes

Loading…