Hexamethylenetetramine → 1-Amino-3-(3,4-dichlorophenyl)-3-methylbutan-2-one hydrobromide

HRID 1627338ノート

反応式

HRID 1627338 の反応式
[Br:1][CH2:2][C:3](=[O:15])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)([CH3:6])[CH3:5].C1N2CN3CN(C2)C[N:17]1C3>C(Cl)Cl>[BrH:1].[NH2:17][CH2:2][C:3](=[O:15])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)([CH3:6])[CH3:5]

参加物

4

反応物 2

HCID 4101HexamethylenetetramineHCID 212583981-Bromo-3-(3,4-dichlorophenyl)-3-methylbutan-2-one

生成物 1

HCID 667410091-Amino-3-(3,4-dichlorophenyl)-3-methylbutan-2-one hydrobromide収率 158.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1-bromo-3-(3,4-dichlorophenyl)-3-methylbutan-2-one (4.0 g, 13 mmol) and HMTA (hexamethylenetetramine, 2.0 g, 14 mmol) in DCM (25 mL) was stirred 48 h at room temperature. The volatiles were evaporated in vacuo. The crude material was dissolved in EtOH (80 mL) and combined with conc HCl (40 mL). The resulting mixture was heated at reflux 2 h, cooled to room temperature, and concentrated in vacuo to give 1-amino-3-(3,4-dichlorophenyl)-3-methylbutan-2-one hydrobromide (6.75 g), which was used in the next reaction without purification. 1H NMR (400 MHz, DMSO-d6) δ 8.00 (bs, 3H), 7.61 (d, 1H), 7.52 (d, 1H), 7.29 (dd, 1H), 3.94 (m, 2H), 1.47 (s, 6H).

後処理

  1. customThe volatiles were evaporated in vacuo
  2. dissolutionThe crude material was dissolved in EtOH (80 mL)
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux 2 h
  5. temperaturecooled to room temperature
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-500becc97c194af99e23470c9e1eb63d
出典データセット
uspto-grants-2014_07
特許番号
US08785488B2

反応ノート

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