Dicyclohexylcarbodiimide → HCID 178418537, compound

HRID 4162

Reaction equation

HRID 4162 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14]([SH:15])=[N:13][N:12]=[N:11]2)[CH:7]=[CH:8][CH:9]=1)([OH:3])=O.[CH:16]([NH:18][NH:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)=[O:17].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[SH:15][C:14]1[N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:1](=[O:3])[NH:24][C:23]3[CH:22]=[CH:21][C:20]([NH:19][NH:18][CH:16]=[O:17])=[CH:26][CH:25]=3)[CH:5]=2)[N:11]=[N:12][N:13]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 113189Hydrazinecarboxaldehyde, 2-(4-aminophenyl)-HCID 178418535HCID 178418535, compound

Product 1

HCID 178418537HCID 178418537, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 50 ml of dimethylformamide were dissolved 11.1 g of 1-(3-carboxyphenyl)-5-mercaptotetrazole and 7.6 g of 4-(2-formylhydrazino)aniline, and a solution of 10.3 g of dicyclohexylcarbodiimide in 10 ml of dimethylformamide was added dropwise to the solution at 0° C. in a nitrogeneous atmosphere over about 30 minutes. After the addition, the mixture was stirred at room temperature for 3 hours. The precipitated dicyclohexylurea was separated by filtration, and the filtrate was added to 500 ml of ice-water while stirring. The thus precipitated crystals were filtered, washed with water and dispersed in 100 ml of hot methanol. The dispersion was allowed to cool to room temperature and filtered. The filtrate was washed with methanol to obtain 4.5 g of the desired compound. Melting point: 202° C. (with decomposition).

Workup

  1. additionAfter the addition
  2. customThe precipitated dicyclohexylurea was separated by filtration
  3. additionthe filtrate was added to 500 ml of ice-water
  4. stirringwhile stirring
  5. filtrationThe thus precipitated crystals were filtered
  6. washwashed with water
  7. additiondispersed in 100 ml of hot methanol
  8. temperatureto cool to room temperature
  9. filtrationfiltered
  10. washThe filtrate was washed with methanol

Sources & evidence

ORD record
ord-91b5da6b753c4d87a85d7b0c1e08baeb
Source dataset
uspto-grants-1988_02
Patent number
US04724199

Linked notes

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