Benzoyl isothiocyanate → HCID 178523941, compound

HRID 597219Notes

Reaction equation

HRID 597219 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][S:7][CH2:8][CH2:9][NH2:10])[N:3]=[CH:2]1.[C:11]([N:19]=[C:20]=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)(Cl)Cl>[C:11]([NH:19][C:20]([NH:10][CH2:9][CH2:8][S:7][CH2:6][C:4]1[N:3]=[CH:2][NH:1][CH:5]=1)=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 178511469HCID 178511469, compound

Product 1

HCID 178523941HCID 178523941, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(i) A solution of 2-(4-imidazolylmethylthio)ethylamine (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°.

Workup

  1. temperatureunder reflux for one hour
  2. concentrationConcentration
  3. customfollowed by recrystallisation from ethyl acetate-isopropyl acetate

Sources & evidence

ORD record
ord-6bbef1235d7d4d1283a395f2a10a5656
Source dataset
uspto-grants-1977_03
Patent number
US04013659

Reaction notes

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