Ammonium thiocyanate → HCID 22400378, compound

HRID 260723Notes

Reaction equation

HRID 260723 reaction equation
Cl.[Cl:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].[S-:11][C:12]#[N:13].[NH4+]>O>[Cl:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:12]([NH2:13])=[S:11]

Participants

4

Reactant 2

HCID 15666Ammonium thiocyanateHCID 186709221-(2-Chlorophenyl)methanamine--hydrogen chloride (1/1)

Product 1

HCID 22400378HCID 22400378, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-chlorobenzylamine hydrochloride (41 g, 0.23 mol) and ammonium thiocyanate (19.28 g, 0.253 mol) in water (170 mL) was heated on the steam bath for 18 hours. This mixture was concentrated in vacuo, and the residue was taken up in toluene (1 L) and azeotroped with a Dean-Stark head. The residue was triturated with wet diethyl ether to provide 27.6 g (60%) of 1-(2-chlorophenyl)methyl thiourea. The product was recrystallized from ethanol; mp 120°-122° C.

Workup

  1. concentrationThis mixture was concentrated in vacuo
  2. customazeotroped with a Dean-Stark head
  3. customThe residue was triturated with wet diethyl ether

Sources & evidence

ORD record
ord-3953e9b7c30c4e5e8fe42d37f310e41c
Source dataset
uspto-grants-1996_06
Patent number
US05530017

Reaction notes

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