Dimethylformamide → 1-PHENYL-2-THIOBIURET

HRID 903907Notes

Reaction equation

HRID 903907 reaction equation
[C:1]1(N=C=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]([NH2:13])=[S:12].C[N:15](C)[CH:16]=[O:17]>>[C:1]1([NH:10][C:11]([NH:13][C:16]([NH2:15])=[O:17])=[S:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7672Phenyl isocyanateHCID 2723790Thiourea

Product 1

HCID 35715781-PHENYL-2-THIOBIURET

Procedure

As the first step in the reaction, phenyl isocyanate, 119 grams (1 mole) is added in one portion with swirling to a warm solution of 83.73 grams (1.1 mole) of thiourea in 120 milliliters of dry dimethylformamide and the resulting solution heated for three hours. Thereafter, the solution is cooled, a mixture of ice and ice water cautiously added and the vessel scratched to induce crystallization of the desired intermediate N-phenylthioimidodicarbonic diamide. After crystallization starts, additional ice water (to about 1 liter) is added. The crystals which form are then recovered, washed with water and recrystallized from methanol to obtain 127 grams of a N-phenylthioimidodicarbonic diamide intermediate product, m.p. 176°-180° C.

Workup

  1. additionis added in one portion
  2. temperaturethe resulting solution heated for three hours
  3. temperatureThereafter, the solution is cooled
  4. additioncautiously added
  5. customcrystallization of the desired intermediate N-phenylthioimidodicarbonic diamide
  6. customAfter crystallization
  7. additionadditional ice water (to about 1 liter) is added
  8. customThe crystals which form are then recovered
  9. washwashed with water
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ae28ff2c67da4d8d91fed31480d6bfe7
Source dataset
uspto-grants-1980_10
Patent number
US04229462

Reaction notes

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