Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 2372690Notes

Reaction equation

HRID 2372690 reaction equation
C(C1C=CC2NN=NC=2C=1)(O)=[O:2].[CH:13]1([N:19]=[C:20]=[N:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>CN(C)C=O>[C:20]([NH:19][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)([NH:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:2]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 178524184HCID 178524184, compound

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 50 ml of dimethylformamide were dissolved 8.1 g of 5-carboxybenzotriazole and 15.3 g of the amino compound obtained in above step 4-(2) and while stirring the solution at 0° C. in a nitrogen gas atmosphere, 5 ml of dimethylformamide solution containing 10.3 g of dicyclohexylcarbodiimide were added dropwise to the solution over a period of 15 minutes. After stirring the mixture for one hour, the mixture-was further stirred for 2 hours at 25° C. Then, dicyclohexylurea formed was removed by filtration and the filtrate thus obtained was added to 1.5 liters of ice water. Crude crystals thus deposited were collected by filtration and dispersed in 100 ml of isopropanol for 15 minutes under heating. The reaction mixture was cooled to room temperature and filtered to provide 12.1 g of desired Compound 201 having a melting point of from 196° C. to 199° C. (decompd.) with the yield of 54%.

Workup

  1. customobtained in above step 4-(2)
  2. additionwere added dropwise to the solution over a period of 15 minutes
  3. stirringthe mixture-was further stirred for 2 hours at 25° C

Sources & evidence

ORD record
ord-857f4e826b59435caca2106b6090fcd5
Source dataset
uspto-grants-1992_03
Patent number
US05100761

Reaction notes

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