Sulfuric Acid → N,N-Bis(2-methylphenyl)thiourea

HRID 1164137Notes

Reaction equation

HRID 1164137 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+]>ClC1C=CC=CC=1C>[C:3]1([CH3:8])[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:15]([NH2:16])=[S:14].[C:3]1([CH3:8])[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8])[C:15]([NH2:16])=[S:14]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 7242O-ToluidineHCID 15666Ammonium thiocyanate

Product 2

HCID 2787703N-(2-Methylphenyl)thioureaHCID 22266619N,N-Bis(2-methylphenyl)thioureaYield 4%

Reagents, catalysts & solvents 1

HCID 72382-ChlorotolueneSolvent

Procedure

In accordance with the process of Example 1 except using 107.2 g of o-toluidine, 250 ml of o-chlorotoluene, 51.6 g of conc. sulfuric acid and 87.5 g of ammonium thiocyanate and reacting them at 90° to 100° C. for 10 hours to obtain o-tolylthiourea having a purity of 95.8% (4.0% of N,N-di-o-tolylthiourea) in an yield of 70.6% as a pure product. The separation of ditolylthiourea was not satisfactory and the yield was low.

Workup

  1. customat 90° to 100° C.
  2. customfor 10 hours

Sources & evidence

ORD record
ord-2872e61fe74b412b985ea18df30d1c77
Source dataset
uspto-grants-1983_01
Patent number
US04367345

Reaction notes

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