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

HRID 2393116

Reaction equation

HRID 2393116 reaction equation
[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]

Participants

9

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-79d6a59a8f1745808545cec4d6d4866a
Source dataset
uspto-grants-1998_09
Patent number
US05804586

Linked notes

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