Phenyl Isothiocyanate → N-(1-methylimidazol-2-yl)-N'-phenylthiourea

HRID 2052066Notes

Reaction equation

HRID 2052066 reaction equation
Cl.[NH2:2][C:3]1[N:4]([CH3:8])[CH:5]=[CH:6][N:7]=1.[OH-].[Na+].[C:11]1([N:17]=[C:18]=[S:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[CH3:8][N:4]1[CH:5]=[CH:6][N:7]=[C:3]1[NH:2][C:18]([NH:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[S:19]

Participants

5

Reactant 3

HCID 7673Phenyl IsothiocyanateHCID 14798Sodium HydroxideHCID 101540761-Methyl-1H-imidazol-2-amine hydrochloride

Product 1

HCID 20378498N-(1-methylimidazol-2-yl)-N'-phenylthiourea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 4.8 g (0.036 mole) sample of 2-amino-1-methylimidazole hydrochloride is suspended in 20 ml of methylene chloride and stirred with 10 ml of 50% NaOH. The organic layer is separated and the aqueous layer is extracted twice with 20 ml portions of fresh methylene chloride. The combined organic extracts are dried over K2CO3 and filtered. The filtrate is treated with 4.86 g (0.036 mole) of phenyl isothiocyanate. The solution is heated under reflux for 4 hr. Evaporation of the solvent in vacuo followed by recrystallization of the residue from acetone-ether (1:1) and MeOH-ether (1:1) gives the product, N-(1-methylimidazol-2-yl)-N'-phenylthiourea; m.p. 170°-172° C.

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted twice with 20 ml portions of fresh methylene chloride
  3. dry with materialThe combined organic extracts are dried over K2CO3
  4. filtrationfiltered
  5. temperatureThe solution is heated
  6. temperatureunder reflux for 4 hr
  7. customEvaporation of the solvent in vacuo
  8. customfollowed by recrystallization of the residue from acetone-ether (1:1) and MeOH-ether (1:1)

Sources & evidence

ORD record
ord-af760901bfa941ffb6f2c35fc0480038
Source dataset
uspto-grants-1980_01
Patent number
US04182865

Reaction notes

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