Sodium Carbonate → 1-(3-Amino-2-methylaminophenyl) 3-mesitylthiourea

HRID 2235532Notes

Reaction equation

HRID 2235532 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][C:4]=1[NH2:10].C(=O)([O-])[O-].[Na+].[Na+].[N:17]([C:20]1[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=1[CH3:28])=[C:18]=[S:19]>C(O)C>[NH2:10][C:4]1[C:3]([NH:2][CH3:1])=[C:8]([NH:9][C:18]([NH:17][C:20]2[C:21]([CH3:28])=[CH:22][C:23]([CH3:27])=[CH:24][C:25]=2[CH3:26])=[S:19])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1386592,4,6-Trimethylphenyl isothiocyanateHCID 12296380N2-Methylbenzene-1,2,3-triamine

Product 1

HCID 866129961-(3-Amino-2-methylaminophenyl) 3-mesitylthioureaYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture containing 0.25 g (1.82 mmol) of N2-methylbenzene-1,2,3-triamine and 0.40 g (3.7 mmol) of sodium carbonate in ethanol was added 0.32 g (1.86 mmol) of 2-isothiocyanato-1,3,5-trimethylbenzene. The reaction was heated at reflux and the solvent was removed under reduced pressure. Purification of the residue via Biotage chromatography eluting with 20% ethyl acetate/dichloromethane gave 0.34 g (60%) of product.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux
  3. customthe solvent was removed under reduced pressure
  4. customPurification of the residue via Biotage chromatography
  5. washeluting with 20% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-c8d35f04a34d41eb8767b5da6273390f
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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