Sulfuric Acid → p-Tolylthiourea

HRID 1769018

Reaction equation

HRID 1769018 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[S-:14][C:15]#[N:16].[NH4+].O.N>C1(C)C=CC=CC=1>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:15]([NH2:16])=[S:14])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 1118Sulfuric Acid2×HCID 7813p-ToluidineHCID 15666Ammonium thiocyanateHCID 12896473Azane;hydrate

Product 1

HCID 722833p-TolylthioureaYield 78.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

10.7 g of 4-toluidine was added dropwise to 27% aqueous sulfuric acid solution which contains 5.4 g of sulfuric acid. After the reaction mixture was heated to 75° C., 8.4 g of ammonium thiocyanate in a solid state was slowly added thereto. Upon complete addition, the reaction mixture was stirred for 20 hours at 80° C. to 90° C. After adding toluene, the whole mixture was refluxed for one hour, cooled to room temperature and then adjusted to pH 7.5 to 8 by slowly adding ammonia water. The resulting white solid was filtered, washed once with each of water and toluene and then dried under reduced pressure to obtain the title compound as a white solid (Yield: 78.5%).

Workup

  1. additionUpon complete addition
  2. temperaturethe whole mixture was refluxed for one hour
  3. temperaturecooled to room temperature
  4. filtrationThe resulting white solid was filtered
  5. washwashed once with each of water and toluene
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-b9b8b619343f4e90b7e36e946562ce05
Source dataset
uspto-grants-1995_01
Patent number
US05380735

Linked notes

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