Water → 3,5-Dichlorophenylthiourea

HRID 986393Notes

Reaction equation

HRID 986393 reaction equation
[S-:1][C:2]#[N:3].[NH4+:4].C(Cl)(=O)C1C=CC=CC=1.[Cl:14][C:15]1[CH:16]=[C:17](NC2C=CC=CC=2)[CH:18]=[C:19]([Cl:21])[CH:20]=1.O>CC(C)=O>[Cl:14][C:15]1[CH:16]=[C:17]([NH:3][C:2]([NH2:4])=[S:1])[CH:18]=[C:19]([Cl:21])[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 190041313,5-Dichloro-N-phenylaniline

Product 1

HCID 27375393,5-DichlorophenylthioureaYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a mixture of 4 liters of acetone and 110 g (1.5 moles) of ammonium thiocyanate are added dropwise 173 g (1.23 moles) of benzoyl chloride. The reaction mixture is then heated for a further 15 minutes. Next, 200 g (1.23 moles) of 3,5-dichlorophenyl aniline dissolved in 200 ml of acetone are added. The mixture is then heated for a further 30 minutes, cooled and poured into 4 liters of water. The precipitate is collected and rinsed with 1 liter of water. The crystals are mixed with 2 liters of water containing 50 g of sodium hydroxide. The mixture is heated for 30 minutes and then cooled. The precipitate is collected to give 238 g (88%) of N-[3,5-dichlorophenyl]thiourea, m.p. 180° C.

Workup

  1. temperatureThe reaction mixture is then heated for a further 15 minutes
  2. additionare added
  3. temperatureThe mixture is then heated for a further 30 minutes
  4. temperaturecooled
  5. customThe precipitate is collected
  6. washrinsed with 1 liter of water
  7. additionThe crystals are mixed with 2 liters of water containing 50 g of sodium hydroxide
  8. temperatureThe mixture is heated for 30 minutes
  9. temperaturecooled
  10. customThe precipitate is collected

Sources & evidence

ORD record
ord-b7ba719a62604d1993af4090073f432e
Source dataset
uspto-grants-1987_12
Patent number
US04713382

Reaction notes

Loading…