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

HRID 1442643

반응식

HRID 1442643 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-6fd098a910c04dc3a2df9164f9949f82
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659284B2

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