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Sodium Azide → HCID 22929889, compound

HRID 1295928
Notes
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Reaction equation

HRID 1295928 reaction equation
Br[CH2:2][C:3]1[C:15]([C:16]#[N:17])=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:5]([O:18][CH2:19][CH3:20])[CH:4]=1.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:21]([CH2:2][C:3]1[C:15]([C:16]#[N:17])=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:5]([O:18][CH2:19][CH3:20])[CH:4]=1)=[N+:22]=[N-:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 22929911HCID 22929911, compound

Product 1

HCID 22929889HCID 22929889, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

After dissolving tert-butyl 4-(bromomethyl)-5-cyano-2-ethoxybenzoate (2.20 g, 70% purity) in dimethylformamide (25 ml), sodium azide (2.1 g) was added and the mixture was stirred at 50° C. for 30 minutes. It was then diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated to yield the title compound (1.913 g).

Workup

  1. additionwas added
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b4f441bf928c4a738fcf8fe3e0a74425
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07244730B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes