1-Tert-butyl-4-(isothiocyanatomethyl)benzene → N-(4-t-Butylbenzyl)-N'-{1-methyl-1-[4-(methylsulfonylamino)phenyl]ethyl}thiourea

HRID 238941Notes

Reaction equation

HRID 238941 reaction equation
[CH3:1][C:2]([NH:15]C(=O)OCC1C=CC=CC=1)([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1)[CH3:3].[H][H].[C:28]([C:32]1[CH:41]=[CH:40][C:35]([CH2:36][N:37]=[C:38]=[S:39])=[CH:34][CH:33]=1)([CH3:31])([CH3:30])[CH3:29]>[Pd].CO>[C:28]([C:32]1[CH:41]=[CH:40][C:35]([CH2:36][NH:37][C:38]([NH:15][C:2]([CH3:3])([C:4]2[CH:5]=[CH:6][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:8][CH:9]=2)[CH3:1])=[S:39])=[CH:34][CH:33]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 3

HCID 148010411-Tert-butyl-4-(isothiocyanatomethyl)benzeneHCID 69527699Benzyl N-{1-Methyl-1-[4-(methylsulfonylamino)phenyl]ethyl}carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 11212675N-(4-t-Butylbenzyl)-N'-{1-methyl-1-[4-(methylsulfonylamino)phenyl]ethyl}thioureaYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of Benzyl N-{1-Methyl-1-[4-(methylsulfonylamino)phenyl]ethyl}carbamate (21-1, 0.5 mmol) and 5% palladium on carbon (100 mg) in MeOH (10 mL) was hydrogenated under a rubber balloon of hydrogen for 1 h. After the solvent was evaporated by rotary evaporator, the residue was dissolved in DMF (5 mL) and treated with 4-t-butylbenzyl isothiocyanate (0.5 mmol). After being stirred overnight, the mixture went to aqueous work-up and the residue was purified by column chromatography on silica gel with EtOAc:hexanes as eluant to afford N-(4-t-Butylbenzyl)-N′-{1-methyl-1-[4-(methylsulfonylamino)phenyl]ethyl}thiourea (21-7, CHK-593)

Workup

  1. customAfter the solvent was evaporated by rotary evaporator
  2. dissolutionthe residue was dissolved in DMF (5 mL)
  3. customthe residue was purified by column chromatography on silica gel with EtOAc

Sources & evidence

ORD record
ord-79e35091780e4bd38f026607a396788d
Source dataset
uspto-grants-2014_02
Patent number
US08642657B2

Reaction notes

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