Dicyclohexylcarbodiimide → HCID 23250757, compound

HRID 1623476Notes

Reaction equation

HRID 1623476 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[C:9](O)(=[O:13])[C:10]#[C:11][CH3:12].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:13])[C:10]#[C:11][CH3:12]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 119952-IodoanilineHCID 685352-Butynoic acid

Product 1

HCID 23250757HCID 23250757, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-iodo-phenylamine (10 g, 45.7 mmol) and but-2-ynoic acid (4.6 g, 54.8 mmol) in dichloromethane (50 ml) was cooled to 0° C. Then 1,3-dicyclohexylcarbodiimide (14 g, 68.6 mmol) was added. After stirring for 3 hours at room temperature, the mixture was washed with water (20 ml). The organic layer was dried over sodium sulfate and concentrated to give the crude product but-2-ynoic acid (2-iodo-phenyl)-amide (13.0 g, 100%) as a yellow solid which was used in next step without purification. MS calcd. for C10H8INO 285.1, obsd. (ESI+) [(M+H)+] 286.0.

Workup

  1. washthe mixture was washed with water (20 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f65413ed659b478f9a80b19859da9e5f
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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