Sulfuric Acid → N-(2-Methylphenyl)thiourea

HRID 1164136Notes

Reaction equation

HRID 1164136 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[S-:14][C:15]#[N:16].[NH4+]>CO>[C:3]1([CH3:8])[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:15]([NH2:16])=[S:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7242O-ToluidineHCID 15666Ammonium thiocyanate

Product 1

HCID 2787703N-(2-Methylphenyl)thioureaYield 89.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In a reactor, 107.2 g of o-toluidine and 250 ml of methanol were charged and 54 g of conc. sulfuric acid was charged with stirring and 87.5 g of ammonium thiocyanate was admixed with the mixture. The mixture was heated to reflux methanol for 20 hours and the precipitate was separated by a filtration and the filtrate was concentrated and washed with water and dried to obtain 149.6 g of o-tolylthiourea. The product was analyzed by a high speed liquid chromatography to find a purity of 74.6% and an yield of 67.1% as a pure product. The purity and the yield were too low.

Workup

  1. temperatureThe mixture was heated
  2. customthe precipitate was separated by a filtration
  3. concentrationthe filtrate was concentrated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-0af0bffe2f0647a7805f02993c9ae8ce
Source dataset
uspto-grants-1983_01
Patent number
US04367345

Reaction notes

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