Chlorosuccinimide → HCID 59030440, compound

HRID 502279Notes

Reaction equation

HRID 502279 reaction equation
[CH:1]([O:4][C:5](=[O:24])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[C:17]([O:22][CH3:23])[CH:16]=3)=[CH:9][CH:8]=1)([CH3:3])[CH3:2].[Cl:25]N1C(=O)CCC1=O>CN(C=O)C.O>[CH:1]([O:4][C:5](=[O:24])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[NH:14][C:15]3[C:20]([C:21]=2[Cl:25])=[CH:19][CH:18]=[C:17]([O:22][CH3:23])[CH:16]=3)=[CH:11][CH:12]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 59030420HCID 59030420, compound

Product 1

HCID 59030440HCID 59030440, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To [4-(6-Methoxy-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester (11.3 g, 34.9 mmol) in DMF (50 mL) was added a solution of N-chlorosuccinimide (5 g, 37.4 mmol) dropwise over 20 minutes and the mixture stirred at room temperature for 1 h. The reaction mixture was diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O and brine and then dried, concentrated and triturated with ether to provide [4-(3-chloro-6-Methoxy-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester (10.65 g, 85%) as a tan solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with H2O and brine
  3. customdried
  4. concentrationconcentrated
  5. customtriturated with ether

Sources & evidence

ORD record
ord-35829724882b406280f36ed547dbbc3c
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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