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

HRID 238941ノート

反応式

HRID 238941 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-79e35091780e4bd38f026607a396788d
出典データセット
uspto-grants-2014_02
特許番号
US08642657B2

反応ノート

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