Sodium Azide → Methyl 4-(azidoacetyl)benzoate

HRID 606586Notes

Reaction equation

HRID 606586 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:13])[CH2:11]Br)=[CH:6][CH:5]=1.[N-:15]=[N+:16]=[N-:17].[Na+]>C(O)C.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:13])[CH2:11][N:15]=[N+:16]=[N-:17])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 13612771Methyl 4-(2-bromoacetyl)benzoate

Product 1

HCID 71414038Methyl 4-(azidoacetyl)benzoateYield 76.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
4 °C

Procedure

4-(2-Bromo-acetyl)-benzoic acid methyl ester (15.5 mmol) was dissolved in ethanol (120 ml) and acetic acid (4.8 ml). Sodium azide (31 mmol) was added and the reaction stirred at 4° C. overnight. The ethanol was removed and the mixture diluted with ethyl acetate (100 ml). The organic layer was washed with saturated sodium hydrogen carbonate (2'50 ml) and dried (MgSO4). The solvent was removed in vacuo to give a yellow solid, which was re-crystallized from ethanol to give the title compound as a pale yellow solid (2.6 g). IR 2117 cm−1

Workup

  1. customThe ethanol was removed
  2. additionthe mixture diluted with ethyl acetate (100 ml)
  3. washThe organic layer was washed with saturated sodium hydrogen carbonate (2'50 ml) and
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customto give a yellow solid, which
  7. customwas re-crystallized from ethanol

Sources & evidence

ORD record
ord-cf1b47fb6dfd48d9ae36a1373b1a98e1
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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