Benzoyl chloride → 1-(2,6-Dibromophenyl)thiourea

HRID 839621Notes

Reaction equation

HRID 839621 reaction equation
C(Cl)(=O)C1C=CC=CC=1.[S-:10][C:11]#[N:12].[NH4+].[Br:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[C:16]=1[NH2:17].NC(N)=S>CC(C)=O>[Br:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[C:16]=1[NH:17][C:11]([NH2:12])=[S:10]

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 690982,6-DibromoanilineHCID 2723790Thiourea

Product 1

HCID 124068471-(2,6-Dibromophenyl)thiourea

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

A solution of 4.6 ml. of benzoyl chloride in 10 ml. of acetone was added over a period of 5 minutes to a solution of 3.32 g. of ammonium thiocyanate in 60 ml. of dry acetone at reflux. The resulting solution was refluxed for 10 minutes and a solution of 10.0 g. of 2,6-dibromoaniline in 40 ml. of acetone was added over a period of 10 minutes. After 15 minutes at reflux, the reaction mixture was poured onto 300 ml. of water and filtered. The resulting solid was suspended in 30 ml. of 10% sodium hydroxide and boiled for 10 minutes. The clear solution was acidified, neutralized to pH 8 with ammonia and filtered, giving 12.0 g. (97%) of 1-(2,6-dibromophenyl(thiourea, m.p. 186°-189°. Recrystallization from aqueous methanol gave the analytical sample, m.p. 192°-193°.

Workup

  1. temperatureThe resulting solution was refluxed for 10 minutes
  2. temperatureAfter 15 minutes at reflux
  3. additionthe reaction mixture was poured onto 300 ml
  4. filtrationof water and filtered
  5. filtrationfiltered
  6. customgiving 12.0 g
  7. customRecrystallization from aqueous methanol
  8. customgave the analytical sample, m.p. 192°-193°

Sources & evidence

ORD record
ord-f2dd8e05ac3b4a739cbe2b8cc32ca423
Source dataset
uspto-grants-1978_06
Patent number
US04096276

Reaction notes

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