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

HRID 238941노트

반응식

HRID 238941 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-79e35091780e4bd38f026607a396788d
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642657B2

반응 노트

불러오는 중…