Ammonia → N-(Phenylmethyl)thiourea

HRID 1585559Notes

Reaction equation

HRID 1585559 reaction equation
[CH2:1]([N:8]=[C:9]=[S:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:11].O>C1COCC1>[CH2:1]([NH:8][C:9]([NH2:11])=[S:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 2346Benzyl Isothiocyanate

Product 1

HCID 737375N-(Phenylmethyl)thioureaYield 108.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

96.3 g (366 mmoles) of benzylisothiocyanate were dissolved in 100 ml of THF and treated with 44.2 ml (732 mmoles) of 32% ammonia solution. After 0.5 hour at 40-45° C., 300 ml of water were added and the THF removed in vacuo. The gummy suspension is treated with 200 ml of ether, the crystals collected and washed with water and ether. Suspension in 30 ml of methylenechloride and collection gave 65.77 g (64.2%) of benzyl-2-thiourea with mp 144-5° C.

Workup

  1. customthe THF removed in vacuo
  2. additionThe gummy suspension is treated with 200 ml of ether
  3. customthe crystals collected
  4. washwashed with water and ether
  5. customSuspension in 30 ml of methylenechloride and collection

Sources & evidence

ORD record
ord-d300d6ced4ef40a4a87ce9f5da0fcb15
Source dataset
uspto-grants-1999_08
Patent number
US05939422

Reaction notes

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