Cyclopropanecarbonyl chloride → Cyclopropanecarboxylic acid (2-cyano-ethyl)-(3-iodo-phenyl)-amide

HRID 963411

Reaction equation

HRID 963411 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH2:10][C:11]#[N:12])[CH:5]=[CH:6][CH:7]=1.[CH:13]1([C:16](Cl)=[O:17])[CH2:15][CH2:14]1>C(Cl)Cl.C(N(CC)CC)C>[C:11]([CH2:10][CH2:9][N:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=1)[C:16]([CH:13]1[CH2:15][CH2:14]1)=[O:17])#[N:12]

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 190816343-(3-Iodo-phenylamino)-propionitrile

Product 1

HCID 53642965Cyclopropanecarboxylic acid (2-cyano-ethyl)-(3-iodo-phenyl)-amideYield 95.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

1.0 g of 3-(3-iodo-phenylamino)-propionitrile are dissolved in a mixture of 25 ml of methylene chloride and 0.45 ml of triethylamine and treated dropwise at 0° with a solution of 0.42 g of cyclopropanecarbonyl chloride in 5 ml of methylene chloride. The solution is stirred at room temperature for a further 2 hrs., then poured into ice-water and extracted three times with ethyl acetate. Concentration yields 1.19 g of crude cyclopropanecarboxylic acid (2-cyano-ethyl)-(3-iodo-phenyl)-amide which is used in Example 12av) without further purification. Yield: 95%.

Workup

  1. extractionextracted three times with ethyl acetate
  2. concentrationConcentration

Sources & evidence

ORD record
ord-5b26c1d082394913b9e14b0220a5dd4c
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Linked notes

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