Water → HCID 21054852, compound

HRID 2376822Notes

Reaction equation

HRID 2376822 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:20][NH:21][C:22](=O)[O:23]C1C=CC=CC=1.O>CN(C)C=O>[CH3:20][NH:21][C:22]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([O:10][CH2:3][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)=[CH:19][CH:18]=2)[CH:14]=[CH:15]1)=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 146245-BenzyloxyindoleHCID 16034Phenyl MethylcarbamateHCID 24758Sodium hydride

Product 1

HCID 21054852HCID 21054852, compoundYield 93.41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (2.212 g, 55.30 mmol, 60% in oil) was suspended in N,N-dimethylformamide (100 ml), 5-benzyloxyindole (10.29 g, 46.09 mmol) was added thereto while stirred at room temperature, and the reaction mixture was stirred at room temperature for 40 minutes. The reaction mixture was cooled with an ice water bath, and phenyl N-methylcarbamate (8.360 g, 55.30 mmol) was added. After the reaction mixture was stirred for 30 minutes, the solution was stirred at room temperature for 2.5 hours. After water was added to the reaction mixture and the reaction mixture was stirred at room temperature for 1 hour, the obtained crystals were filtered off, then these crystals were sequentially washed with water and diethyl ether, and dried under aeration to yield the title compound (12.07 g, 43.06 mmol, 93.41%) as pale yellow crystals.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 40 minutes
  2. temperatureThe reaction mixture was cooled with an ice water bath
  3. stirringAfter the reaction mixture was stirred for 30 minutes
  4. stirringthe solution was stirred at room temperature for 2.5 hours
  5. stirringthe reaction mixture was stirred at room temperature for 1 hour
  6. filtrationthe obtained crystals were filtered off
  7. washthese crystals were sequentially washed with water and diethyl ether
  8. customdried under aeration

Sources & evidence

ORD record
ord-326f16f425434b94b1d01eff945cfcdb
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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