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

HRID 2393459

反応式

HRID 2393459 の反応式
[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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2647db0c64564123b3bfc870460661dd
出典データセット
uspto-grants-1998_09
特許番号
US05807868

関連ノート

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