Phenyl isocyanate → HCID 59335056, compound

HRID 1517931Notes

Reaction equation

HRID 1517931 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH2:17][CH2:16]3)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:36]1([N:42]=[C:43]=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:43](=[O:44])[NH:42][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:17][CH2:16]3)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 11430Potassium CarbonateHCID 59334895HCID 59334895, compound

Product 1

HCID 59335056HCID 59335056, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

990 mg tert.butyl [(3,5-dichloro-phenylsulphonyl)-(2,3-dihydro-1H-indol-5-yl)-amino]-acetate are dissolved in 10 ml dichloromethane. 598 mg potassium carbonate and 247 μl phenylisocyanate are added. After stirring overnight the solid is filtered off and washed twice with dichloromethane. The combined organic phases are evaporated down in vacuo and the residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 10:1 to 1:2).

Workup

  1. filtrationis filtered off
  2. washwashed twice with dichloromethane
  3. customThe combined organic phases are evaporated down in vacuo
  4. customthe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 10:1 to 1:2)

Sources & evidence

ORD record
ord-4c2d592bae784d609f0d5dd16d10a764
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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