Dicyclohexylcarbodiimide → HCID 178512296, compound

HRID 864486Notes

Reaction equation

HRID 864486 reaction equation
[C:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=S)#[N:2].[C:13]1([NH:19][CH2:20][CH2:21][NH2:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[C:1]([NH:3][C:4]([NH:22][CH2:21][CH2:20][NH:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 742701,2-Ethanediamine, N1-phenyl-HCID 13358277N-Cyano-N'-pyridin-4-ylthiourea

Product 1

HCID 178512296HCID 178512296, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Cyano-N'-4-pyridylthiourea (1.80 g) was suspended in dimethylformamide (5 ml). While stirring in an ice bath N-phenylethylenediamine (1.4 ml) and N,N'-dicyclohexylcarbodiimide (2.50 g) were added, resulting in a clear solution. The mixture was left at room temperature for 3 days, when the suspension formed was evaporated extensively under high vacuum. The residue was triturated repeatedly with ether (15 ml portions), and the residual solid was extracted with 1N hydrochloric acid (50 ml). After filtration, the crude product was precipitated from the filtrate by addition of 9N sodium hydroxide and taken up into ethyl acetate (3×75 ml).

Workup

  1. additionwere added
  2. customresulting in a clear solution
  3. customwhen the suspension formed
  4. customwas evaporated extensively under high vacuum
  5. customThe residue was triturated repeatedly with ether (15 ml portions)
  6. extractionthe residual solid was extracted with 1N hydrochloric acid (50 ml)
  7. filtrationAfter filtration
  8. customthe crude product was precipitated from the filtrate by addition of 9N sodium hydroxide

Sources & evidence

ORD record
ord-2f5c64496bf24f46bd86a4b03a980dc2
Source dataset
uspto-grants-1996_10
Patent number
US05563160

Reaction notes

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