Phenyl isocyanate → N-{6-Oxo-7-[(triphenylmethyl)sulfanyl]heptyl}-N'-phenylurea

HRID 1176839Notes

Reaction equation

HRID 1176839 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:29])[CH2:8][S:9][C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:30]1([N:36]=[C:37]=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[O:29]=[C:7]([CH2:8][S:9][C:10]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:37]([NH:36][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:38]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 670068517-Amino-1-tritylsulfanyl-heptan-2-one

Product 1

HCID 67006722N-{6-Oxo-7-[(triphenylmethyl)sulfanyl]heptyl}-N'-phenylureaYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-amino-1-tritylsulfanyl-heptan-2-one (0.36 g, 0.86 mmol) in dichloromethane (10 mL) was added phenylisocyanate (0.10 ml, 0.92 mmol). The mixture was stirred at room temperature for 2 h. Solvent was then removed in vacuo and the crude product was purified by column chromatography (dichloromethane/MeOH=100/1 to 40/1) to provide 1-(6-Oxo-7-tritylsulfanyl-heptyl)-3-phenyl-urea (0.43 g, 93%).

Workup

  1. customSolvent was then removed in vacuo
  2. customthe crude product was purified by column chromatography (dichloromethane/MeOH=100/1 to 40/1)

Sources & evidence

ORD record
ord-483f92fd2f44485cb6e6dc0152283220
Source dataset
uspto-grants-2010_11
Patent number
US07842835B2

Reaction notes

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