Cyanamide → HCID 178512274, compound

HRID 1939287Notes

Reaction equation

HRID 1939287 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([NH:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=S)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:22]#[C:23][NH2:24].C1(N=C=NC2CCCCC2)CCCCC1.C1(NC(NC2CCCCC2)=S)CCCCC1>C(#N)C.C(N(CC)CC)C>[C:23]([NH:24][C:13]([NH:12][CH2:11][CH2:10][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[N:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)#[N:22]

Participants

7

Reactant 4

HCID 9864CyanamideHCID 10868DicyclohexylcarbodiimideHCID 727200DicyclohexylthioureaHCID 21467376N-(4-Phenoxybutyl)-N'-3-pyridylthiourea

Product 1

HCID 178512274HCID 178512274, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

N-(4-Phenoxybutyl)-N'-3-pyridylthiourea (1.41 g) was dissolved in acetonitrile (10 ml), and cyanamide (400 mg), N,N'dicyclohexylcarbodiimide (1.95 g) and triethylamine (0.08 ml) were added. The mixture was stirred for 3 days at room temperature, when it was filtered, washed with acetonitrile, and ether to yield a solid mixture of the crude product and N,N'-dicyclohexylthiourea. The pure compound was obtained by extracting the mixture with 0.5N hydrochloric acid (16 ml), filtering and re-precipitation by addition of 9N sodium hydroxide to the filtrate.

Workup

  1. filtrationwhen it was filtered
  2. washwashed with acetonitrile, and ether
  3. customto yield
  4. customThe pure compound was obtained
  5. extractionby extracting the mixture with 0.5N hydrochloric acid (16 ml)
  6. filtrationfiltering
  7. customre-precipitation
  8. additionby addition of 9N sodium hydroxide to the filtrate

Sources & evidence

ORD record
ord-a8d4d5cff3a34299a8adda0934c95dc3
Source dataset
uspto-grants-1997_12
Patent number
US05696140

Reaction notes

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