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

HRID 1442643

反応式

HRID 1442643 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-6fd098a910c04dc3a2df9164f9949f82
出典データセット
uspto-grants-2010_02
特許番号
US07659284B2

関連ノート

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