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

HRID 2266401

반응식

HRID 2266401 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1e9175463bb945c39c9c4b4ecdec82de
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858647B2

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