Isopropanol → HCID 178514167, compound

HRID 847836Notes

Reaction equation

HRID 847836 reaction equation
C(O)(C)C.C([NH:13][C:14]([NH:16][CH2:17][CH2:18][S:19][CH2:20][C:21]1[N:22]=[CH:23][NH:24][CH:25]=1)=[S:15])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O>[NH:24]1[CH:25]=[C:21]([CH2:20][S:19][CH2:18][CH2:17][NH:16][C:14]([NH2:13])=[S:15])[N:22]=[CH:23]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 178523941HCID 178523941, compound

Product 1

HCID 178514167HCID 178514167, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4(5)-[(2-aminoethyl)thiomethyl]imidazole (6.0 g.) and benzoyl isothiocyanate (6.0 g.) in chloroform (150 ml.) was heated under reflux for one hour. Concentration followed by recrystallisation from ethyl acetate-isopropyl acetate afforded N-benzoyl-N'-[2-(4-imidazolylmethylthio)-ethyl]thiourea (7.5 g.). An analytically pure sample (from aqueous isopropyl alcohol) had m.p. 126°-128°. (ii) The benzoyl thiourea (6.0 g.) was added to a solution of potassium carbonate (1.4 g.) in water (80 ml.), at 60°. The solution was maintained at this temperature for one hour, concentrated to low bulk and acidified with hydrochloric acid. Benzoic acid was removed by filtration and the filtrate was basified with potassium carbonate and concentrated under reduced pressure. Following extraction with isopropyl alcohl and concentration, the product was crystallised from isopropyl acetate. Recrystallisation from water gave N-[2-(4-imidazolylmethylthio)ethyl]thiourea (2.5 g.) m.p. 135°-137°. (Found: C, 38.9; H, 5.5; N, 26.1; S, 29.6. C7H12N4S2 requires: C, 38.9; H, 5.6; N, 25.9; S, 29.6).

Workup

  1. temperatureThe solution was maintained at this temperature for one hour
  2. concentrationconcentrated to low bulk
  3. customBenzoic acid was removed by filtration
  4. concentrationconcentrated under reduced pressure
  5. extractionextraction
  6. concentrationwith isopropyl alcohl and concentration
  7. customthe product was crystallised from isopropyl acetate
  8. customRecrystallisation from water

Sources & evidence

ORD record
ord-1bb3e039e0234fd198100a292b7239be
Source dataset
uspto-grants-1981_10
Patent number
US04293697

Reaction notes

Loading…