Triethylamine → HCID 16379526, compound

HRID 963416Notes

Reaction equation

HRID 963416 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(CC)CC)C.[CH:16]1([C:19](Cl)=[O:20])[CH2:18][CH2:17]1>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([NH:5][C:19]([CH:16]2[CH2:18][CH2:17]2)=[O:20])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122713-IodoanilineHCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 16379526HCID 16379526, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.53 g of 3-iodoaniline and 2.78 ml of triethylamine are dissolved in 25 ml of methylene chloride and treated dropwise at room temperature with a solution of 1.6 ml of cyclopropane carbonyl chloride in 10 ml of methylene chloride. The mixture is stirred at room temperature for a further 5 hrs., evaporated and poured into 50 ml of water. The mixture is made slightly acid with dil. hydrochloric acid and extracted three times with ethyl acetate. The residue is recrystallized from toluene. 1.47 g of cyclopropanecarboxylic acid (3-iodo-phenyl)-amide are isolated as a colourless solid. Yield: 74%. M.p.=133°.

Workup

  1. custom, evaporated
  2. additionpoured into 50 ml of water
  3. extractionextracted three times with ethyl acetate
  4. customThe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-a858492038a448aea39bebf20662efd5
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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