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Water → N-ethyl-4-azido-3-benzyloxybenzamide

HRID 1717340
Notes
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Reaction equation

HRID 1717340 reaction equation
[N:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([NH:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]=1[OH:15])=[N+:2]=[N-:3].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[N:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([NH:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[N+:2]=[N-:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 866298074-azido-N-ethyl-3-hydroxybenzamide

Product 1

HCID 86629808N-ethyl-4-azido-3-benzyloxybenzamideYield 97%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4-azido-N-ethyl-3-hydroxybenzamide (3.44 g) obtained in Example 133b) in DMF (50 ml) were added benzyl bromide (2.4 ml) and potassium carbonate (2.76 g), and the reaction mixture was stirred at 55° C. for 3.5 hr. The reaction mixture was allowed to cool to room temperature, water was added and the resulting precipitate was collected by filtration and washed with water to give the title compound as a brown powder (4.81 g, 97%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-226d7cff01c14f608e5d0b747184f8d4
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07803822B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes