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Water → HCID 73197958, compound

HRID 2414256
Notes
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Reaction equation

HRID 2414256 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([C:14](=[N:16][OH:17])[CH3:15])=[CH:10][C:3]=1[CH2:4][NH:5][C:6](=[O:9])[O:7][CH3:8].[H-].[Na+].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1.O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([C:14](=[N:16][O:17][CH2:25][C:24]2[CH:27]=[CH:28][C:21]([F:20])=[CH:22][CH:23]=2)[CH3:15])=[CH:10][C:3]=1[CH2:4][NH:5][C:6](=[O:9])[O:7][CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 86641517methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate

Product 1

HCID 73197958HCID 73197958, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
2×
HCID 8857Ethyl AcetateSolvent

Procedure

0.70 g of methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate was dissolved in 10 ml of N,N-dimethylformamide, and 0.13 g of 60% sodium hydride was added thereto under cooling with ice, followed by stirring for 1 hour. 0.57 g of 4-fluorobenzyl bromide was dissolved in 2 ml of N,N-dimethylformamide, which was dropwise added to the reaction mixture under cooling with ice. After completion of the dropwise addition, the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction solution was poured into water, extraction with ethyl acetate was carried out, followed by washing with water, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (Wakogel C-200, eluent: hexane/ethyl acetate=5/1) to obtain 0.75 g of methyl N-{2-chloro-5-[1-(4-fluorobenzyloxyimino)ethyl]benzyl}carbamate (m.p. 101-103° C.) as colorless crystals.

Workup

  1. temperatureunder cooling with ice
  2. additionwhich was dropwise added to the reaction mixture
  3. temperatureunder cooling with ice
  4. additionAfter completion of the dropwise addition
  5. stirringthe mixture was stirred at room temperature for 16 hours
  6. customAfter completion of the reaction
  7. washby washing with water
  8. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (Wakogel C-200, eluent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-8757f696a571466eb340ac5e48daf01e
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06812229B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes