Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1248964Notes

Reaction equation

HRID 1248964 reaction equation
C(O[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23](C1C=C(SC2N(C3C=CC=C(C(O)=O)C=3)N=NN=2)C2C(=CC=CC=2)C=1O)=[O:24])CCCCCCCCCCCCC.C(NN[C:55]1[CH:60]=[CH:59][C:58]([NH2:61])=[CH:57][CH:56]=1)=O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[C:23]([NH:61][CH:58]1[CH2:57][CH2:56][CH2:55][CH2:60][CH2:59]1)([NH:22][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:16]1)=[O:24]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 113189Hydrazinecarboxaldehyde, 2-(4-aminophenyl)-HCID 20146208HCID 20146208, compound

Product 1

HCID 4277N,N'-DicyclohexylureaYield 55.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

13.9 g of 2-(2-tetradecyloxyphenyl)carbamoyl-4-[1-(3-carboxyphenyl)-5-tetrazolylthio]-1-naphthol and 3.0 g of 1-formyl-2-(4-aminophenyl)hydrazine were dissolved in 20 ml of DMF and to the solution was added dropwise with stirring 5 ml of a DMF solution containing 4.1 g of dicyclohexylcarbodiimide at 0° C. under nitrogen atmosphere. After the completion of the addition, the mixture was stirred for 2 hours and then further stirred at room temperature for 2 hours. Dicyclohexylurea formed was removed by filtration and the filtrate was poured into 1.5 liters of water. The crystals thus deposited were collected by filtration and dissolved in 50 ml of DMF. After treating with active carbon the DMF solution was poured into 400 ml of methanol and the crystals thus deposited were collected by filtration to obtain 9.2 g of the desired Compound (15). Yield: 55.5%. Melting Point: 173° to 180° C.

Workup

  1. additionwas added dropwise
  2. additionAfter the completion of the addition
  3. stirringfurther stirred at room temperature for 2 hours

Sources & evidence

ORD record
ord-6ee2a14221f140f4bd4d9a777614e16a
Source dataset
uspto-grants-1986_12
Patent number
US04628024

Reaction notes

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