Ammonia → N-(2-(4-methoxy-3-methylphenyl)ethyl)-1-(2-thienyl)cyclopropanecarboxamide

HRID 2393459

반응식

HRID 2393459 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH2:11])=[CH:5][C:4]=1[CH3:12].C1(N=C=NC2CCCCC2)CCCCC1.[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33]1([C:36](O)=[O:37])[CH2:35][CH2:34]1.ON1C2C=CC=CC=2N=N1.N>O1CCCC1.O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:36]([C:33]2([C:29]3[S:28][CH:32]=[CH:31][CH:30]=3)[CH2:35][CH2:34]2)=[O:37])=[CH:5][C:4]=1[CH3:12]

참가 물질

9

반응물 5

HCID 222AmmoniaHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 64846602-(4-Methoxy-3-methylphenyl)ethan-1-amineHCID 189757061-(Thiophen-2-yl)cyclopropane-1-carboxylic acid

생성물 1

HCID 18975656N-(2-(4-methoxy-3-methylphenyl)ethyl)-1-(2-thienyl)cyclopropanecarboxamide수율 81.5%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

A mixture of 2-(4-methoxy-3-methylphenyl)ethylamine (16 g), triethylamine (1.74 ml), 1,3-dicyclohexylcarbodiimide (8.75 g), 1-(2-thienyl)cyclopropanecarboxylic acid (7 g) and 1-hydroxybenzotriazole (5.6 g) in tetrahydrofuran (95 ml) was stirred for 16 hours. The mixture was poured into water, basified with aqueous ammonia solution and filtered. The filtrate was extracted with ethyl acetate (3×50 ml) and the combined extracts washed with 1M hydrochloric acid and brine then dried and the solvent removed in vacuo. The resulting gum was treated with acetonitrile and insoluble matter filtered off. Evaporation of the filtrate gave crude N-[2-(4-methoxy-3-methylphenyl)ethyl]-1-(2-thienyl)cyclopropanecarboxamide as a solid (10.7 g), which was used without further purification.

후처리

  1. filtrationfiltered
  2. extractionThe filtrate was extracted with ethyl acetate (3×50 ml)
  3. washthe combined extracts washed with 1M hydrochloric acid and brine
  4. customthen dried
  5. customthe solvent removed in vacuo
  6. additionThe resulting gum was treated with acetonitrile and insoluble matter
  7. filtrationfiltered off
  8. customEvaporation of the filtrate

출처 및 근거

ORD 기록
ord-2647db0c64564123b3bfc870460661dd
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05807868

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