Dicyclohexylcarbodiimide → HCID 57237301, compound

HRID 1252631Notes

Reaction equation

HRID 1252631 reaction equation
[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][NH:5][C:4]([CH:16]=[CH:17][C:18]([OH:20])=O)=[CH:3]1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[C:46]([O:50][C:51]([NH:53][NH2:54])=[O:52])([CH3:49])([CH3:48])[CH3:47]>CN(C)C=O>[CH3:47][C:46]([CH3:49])([O:50][C:51]([NH:53][NH:54][C:18](=[O:20])[CH:17]=[CH:16][C:4]1[NH:5][CH:6]=[C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:2](=[O:1])[CH:3]=1)=[O:52])[CH3:48]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 54235107HCID 54235107, compound

Product 1

HCID 57237301HCID 57237301, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2pyridinyl]-2-propenoic acid (1.36 g), 0.75 g of N-hydroxybenzotriazole, 0.01 g of N,N-dimethylaminopyridine and 1.06 g of dicyclohexylcarbodiimide were stirred in 20 ml of dimethylformamide at 0° C. for 20 minutes. 0.66 g of N-(t-butoxycarbonyl)hydrazine was added. After stirring overnight, the formed dicyclohexylurea was filtered off and the filtrate was washed with 10 ml of dimethylformamide. The filtrate was evaporated to dryness and the residue was suspended in 30 ml of water, 1 g of sodium bicarbonate was added, and after stirring, the title compound was isolated by filtration. Recrystallization from dimethylformamide/water gave white crystals. Yield: 1.47 g, melting point 141° C.

Workup

  1. filtrationthe formed dicyclohexylurea was filtered off
  2. washthe filtrate was washed with 10 ml of dimethylformamide
  3. customThe filtrate was evaporated to dryness
  4. addition1 g of sodium bicarbonate was added
  5. stirringafter stirring

Sources & evidence

ORD record
ord-ff35c69c802d4ad98b911b0118aced7c
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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