Sodium Azide → HCID 86632577, compound

HRID 660569Notes

Reaction equation

HRID 660569 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7](=[O:17])[CH:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[I:15]>CN(C=O)C.[Cl-].[Na+].O>[CH3:5][O:6][C:7](=[O:17])[CH:8]([N:1]=[N+:2]=[N-:3])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[I:15]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86632576Bromo-(2-iodophenyl)-acetic Acid Methyl Ester

Product 1

HCID 86632577HCID 86632577, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of NaN3 (10.6 g, 163 mmol) in DMF (100 mL) is added bromo-(2-iodophenyl)-acetic acid methyl ester (19.3 g, 54.4 mmol) and the mixture is stirred at RT for 18 h. Brine is added and the mixture is extracted with ether (10×100 mL). The combined organic layers are washed with brine and dried over sodium sulfate. The solvent is removed under reduced pressure to afford the title compound which is used directly in the next step.

Workup

  1. extractionthe mixture is extracted with ether (10×100 mL)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-c434cc31a8e54fad97456b4d4d059f8c
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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