1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ethyl 4-[(5-cyano-2-benzofuranyl)carbonylamino]phenoxyacetate

HRID 1682654Notes

Reaction equation

HRID 1682654 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([OH:13])=O)=[CH:8][C:7]=2[CH:14]=1)#[N:2].[NH2:15][C:16]1[CH:28]=[CH:27][C:19]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CN(C)C=O.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:27][CH:28]=3)=[O:13])=[CH:8][C:7]=2[CH:14]=1)#[N:2]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 412616Ethyl 2-(4-aminophenoxy)acetateHCID 102360545-cyanobenzofuran-2-carboxylic Acid

Product 1

HCID 18919414Ethyl 4-[(5-cyano-2-benzofuranyl)carbonylamino]phenoxyacetateYield 92.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-Cyano-2-benzofurancarboxylic acid (830 mg, 4.43 mmol) and ethyl 4-aminophenoxyacetate (910 mg, 4.66 mmol) were dissolved in N,N-dimethylformamide (40 ml), and 1-hydroxy-1H-benzotriazole (630 mg, 4.66 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (893 mg, 4.66 mmol) were added. The mixture was stirred at room temperature for 13 hours. Water (100 ml) was added to the reaction mixture. The resulting precipitate was collected by filtration and washed with water to give 1.49 g of ethyl 4-[(5-cyano-2-benzofuranyl)carbonylamino]phenoxyacetate as a colorless solid (92%).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-8b4d487c249f4ece955035ea690e3eb8
Source dataset
uspto-grants-1997_06
Patent number
US05635527

Reaction notes

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