Carbon Disulfide → Metiamide

HRID 372269Notes

Reaction equation

HRID 372269 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[CH:12]1([N:18]=[C:19]=NC2CCCCC2)CCCCC1.C(=S)=[S:28]>N1C=CC=CC=1>[CH3:12][NH:18][C:19]([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:28]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 10868DicyclohexylcarbodiimideHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazole

Product 1

HCID 1548992Metiamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 2-((5-methyl-4-imidazolyl)methylthio)ethylamine (3.42 g 0.02 mol) in dry pyridine (15 ml) was slowly added under dry nitrogen to a stirred solution of N,N'-dicyclohexylcarbodiimide (4.12 g 0.02 mol) and carbon disulphide (20 ml) in dry pyridine (10 ml) at -10°. The mixture was stirred for 4 hours at -10° and 18 hours at room temperature and was filtered. The filtrate was evaporated to dryness and the residue was dissolved in warm acetonitrile and the solution was cooled, filtered and the filtrate was evaporated to dryness. The residue was boiled for five minutes with an excess of aqueous methylamine. The solid which crystallised on cooling was recrystallised from water to give N-methyl-N'-[2-(5-methyl-4-imidazolylmethylthio)ethyl]thiourea.

Workup

  1. filtrationwas filtered
  2. customThe filtrate was evaporated to dryness
  3. dissolutionthe residue was dissolved in warm acetonitrile
  4. temperaturethe solution was cooled
  5. filtrationfiltered
  6. customthe filtrate was evaporated to dryness
  7. waitThe residue was boiled for five minutes
  8. customThe solid which crystallised
  9. temperatureon cooling
  10. customwas recrystallised from water

Sources & evidence

ORD record
ord-d1717f6fb9614bc78686e243b654e867
Source dataset
uspto-grants-1978_05
Patent number
US04090026

Reaction notes

Loading…