Methyl isothiocyanate → HCID 178486098, compound

HRID 66582Notes

Reaction equation

HRID 66582 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3].[CH3:16][N:17]=[C:18]=[S:19]>C(O)C>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:14][CH2:13][CH:12]([NH:15][C:18]([NH:17][CH3:16])=[S:19])[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 178512623HCID 178512623, compound

Product 1

HCID 178486098HCID 178486098, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-guanidino-4-(3-aminocyclopentyl)thiazole (0.3 g.) in ethanol (5 ml.) was added methyl isothiocyanate (0.15 g.) and the mixture heated under reflux for 1 hour. The reaction mixture was evaporated to dryness and the residue subjected to preparative thin layer chromatography on silica gel GF plates (Uniplate, Analtech Inc., Delaware, U.S.A.) using chloroform/methanol/aqueous ammonia (s.g. 0.88) 135:15:1 v/v/v for development. The appropriate region of the chromatogram was eluted with warm ethanol/chloroform (3:1 v/v) and the extract evaporated to give 2-guanidino-4-[3-(3-methylthioureido)cyclopentyl]thiazole as a light brown glass. The n.m.r. spectrum in d6 dimethyl sulphoxide included signals at 1.2-2.2 (m) 2.8 (d, 3H) 4.2 (br m, 1H), 6.27 (s, 1H) and 6.78 (br s, 4H).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1 hour
  3. customThe reaction mixture was evaporated to dryness
  4. washThe appropriate region of the chromatogram was eluted with warm ethanol/chloroform (3:1 v/v)
  5. customthe extract evaporated

Sources & evidence

ORD record
ord-ed5b99a9b9f0463bb3d2a72b612bb07c
Source dataset
uspto-grants-1982_08
Patent number
US04342765

Reaction notes

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