2,4,6-Trimethylphenyl isothiocyanate → 1-(5-Dipropylamino-2-methylphenyl)-3-mesitylthiourea

HRID 2235508Notes

Reaction equation

HRID 2235508 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10][CH3:11])=[CH:4][C:3]=1[NH2:15].[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[N:25]=[C:26]=[S:27]>CO>[CH2:9]([N:8]([CH2:12][CH2:13][CH3:14])[C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:15][C:26]([NH:25][C:18]2[C:17]([CH3:16])=[CH:22][C:21]([CH3:23])=[CH:20][C:19]=2[CH3:24])=[S:27])[CH:4]=1)[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 1386592,4,6-Trimethylphenyl isothiocyanateHCID 629129824-Methyl-N1,N1-dipropyl-benzene-1,3-diamine

Product 1

HCID 866129911-(5-Dipropylamino-2-methylphenyl)-3-mesitylthioureaYield 70.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-Methyl-N1,N1-dipropyl-benzene-1,3-diamine (200 mg, 0.970 mmol) and 2,4,6-trimethylphenylisothiocyanate (215 mg, 1.21 mmol) in methanol (2 ml) was refluxed for 18 h. The solvent was evaporated under vacuum. The residue was triturated with methanol. The solid was collected by filtration and washed with methanol to afford 261 mg of the title compound.

Workup

  1. temperaturewas refluxed for 18 h
  2. customThe solvent was evaporated under vacuum
  3. customThe residue was triturated with methanol
  4. filtrationThe solid was collected by filtration
  5. washwashed with methanol

Sources & evidence

ORD record
ord-e56c59e4da1b4b6fbe4a84d7a669e900
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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