Dimethylformamide → N,N'-Dicyclohexylurea

HRID 400093Notes

Reaction equation

HRID 400093 reaction equation
CN(C)C=[O:4].C1(N2C(C3C=CC=CC=3)CC(=O)N2)C=CC=CC=1.[CH:24]1([N:30]=[C:31]=[N:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:31]([NH:30][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1)([NH:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:4]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 36953731,5-Diphenylpyrazolidin-3-one

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

Into 100 ml of dimethylformamide, 23.8 g of Compound (A), 30.1 g of Compound (B) and 0.8 g of 4-dimethylamino-pyridine were dissolved, and thereto an ethyl acetate 20 ml solution containing 20.6 g of dicyclohexylcarbodiimide was added dropwise in an ice bath. After the dropwise addition, the solution was allowed to react at room temperature over night. Into the reaction solution, 200 ml of ethyl acetate was poured, and dicyclohexylurea obtained was separated by filtration. Into the filtrate, 300 ml of water was poured to perform liquid separation operation. Water washing was performed twice, the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the oily product obtained was subjected to silica gel column chromatography. As a result, from the methylene chloride/ethyl acetate=10/3 fraction, 43 g of Compound (C) was obtained as a pale yellow oily product. ##STR16## Synthesis of Compound (D):

Workup

  1. additionwas added dropwise in an ice bath
  2. additionAfter the dropwise addition
  3. customto react at room temperature over night

Sources & evidence

ORD record
ord-46a28bea654e4c7d9fedeb6812c1b619
Source dataset
uspto-grants-1998_10
Patent number
US05827637

Reaction notes

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