Cyanamide → N-cyano-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]thiourea

HRID 1702481Notes

Reaction equation

HRID 1702481 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][N:11]=[C:12]=[S:13].[N:14]#[C:15][NH2:16].C1CCN2C(=NCCC2)CC1>C(Cl)(Cl)Cl>[C:15]([NH:16][C:12]([NH:11][CH2:10][CH2:9][S:8][CH2:7][C:3]1[N:4]=[CH:5][NH:6][C:2]=1[CH3:1])=[S:13])#[N:14]

Participants

5

Reactant 3

HCID 9864CyanamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 203874262-(5-Methylimidazol-4-ylmethylthio)ethylisothiocyanate

Product 1

HCID 12918615N-cyano-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]thioureaYield 78.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 2-(5-methylimidazol-4-ylmethylthio)ethylisothiocyanate [obtained from its hydrochloride (4.17 g)] in CHCl3 (20 ml) was added to a solution of cyanamide (1.05 g) and DBU (3.80 g) in CHCl3 (50 ml) and stirred overnight. After concentration, the residue was dissolved in water (30 ml) and washed with ether, decolorized with charcoal and acidified to pH 5 with 10% HCl under ice-cooling. The precipitate was filtered, washed with water and dried to give N-cyano-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]thiourea(mono-hydrate, 3.57 g). Yield 78.1%, m.p. 158°-161° C.

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in water (30 ml)
  3. washwashed with ether
  4. temperaturecooling
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-441aadf59ace4f8a810f15513daa0d52
Source dataset
uspto-grants-1983_04
Patent number
US04381395

Reaction notes

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