Potassium Carbonate → HCID 21873334, compound

HRID 723352Notes

Reaction equation

HRID 723352 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:13][CH2:19][CH:18]([O:21][CH3:22])[O:17][CH3:16])=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 228604-BenzyloxyanilineHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 21873334HCID 21873334, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-benzyloxyaniline (10 g), bromoacetaldehyde dimethyl acetal (12.2 g), potassium carbonate (13.8 g) and dimethylformamide (150 mL) was heated at 100° C. for 5 hours. After cooling, the reaction solution was filtered and concentrated. The residue was purified by MPLC (eluent: heptane/ethyl acetate 4:1). The product with the molecular weight of 287.36 (C17H21NO3); MS (ESI): 288 ([M+H]+), was obtained in this way.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction solution was filtered
  3. concentrationconcentrated
  4. customThe residue was purified by MPLC (eluent: heptane/ethyl acetate 4:1)
  5. customMS (ESI): 288 ([M+H]+), was obtained in this way

Sources & evidence

ORD record
ord-3a3e953dce674b899f83d756ba43b2aa
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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