Phenethylamine → 5-chloro-2-methoxy-N-(2-phenylethyl)benzamide

HRID 2266401ノート

反応式

HRID 2266401 の反応式
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH3:21])=[C:15]([CH:19]=1)[C:16](O)=[O:17].C(N(CC)CC)C.F[B-](F)(F)F.C(OC(C(=NOC(N(C)C)=[N+](C)C)C#N)=O)C>CN(C)C=O.C(OCC)(=O)C>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH3:21])=[C:15]([CH:19]=1)[C:16]([NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:17]

参加物

7

反応物 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 769705-Chloro-o-anisic acidHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate

生成物 1

HCID 1185755-chloro-2-methoxy-N-(2-phenylethyl)benzamide収率 90.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3.0 g phenethylamine, 5.0 g 5-chloro-2-methoxy-benzoic acid, and 2.72 ml triethylamine were dissolved in 100 ml dimethylformamide. 8.80 g O-((Ethoxycarbonyl)cyanomethyleneamino)-N,N,N′,N′-tetramethyluronium tetrafluoroborate were added portionwise. The reaction mixture is stirred at room temperature for three hours. 300 ml ethyl acetate were added and the mixture was washed three times with portions of 50 ml saturated NaHCO3 solution and brine. The organic phase was dried over MgSO4 and then the solvent was removed in vacuo to obtain 6.5 g 5-Chloro-2-methoxy-N-phenethyl-benzamide.

後処理

  1. washthe mixture was washed three times with portions of 50 ml saturated NaHCO3 solution and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-1e9175463bb945c39c9c4b4ecdec82de
出典データセット
uspto-grants-2010_12
特許番号
US07858647B2

反応ノート

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