Sodium Azide → 4-Bromocinnamoyl azide

HRID 2068591Notes

Reaction equation

HRID 2068591 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Br:5][C:6]1[CH:16]=[CH:15][C:9]([CH:10]=[CH:11][C:12](Cl)=[O:13])=[CH:8][CH:7]=1>O.CC(C)=O>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([CH:10]=[CH:11][C:12]([N:1]=[N+:2]=[N-:3])=[O:13])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 534112933-(4-Bromophenyl)prop-2-enoyl chloride

Product 1

HCID 539034244-Bromocinnamoyl azideYield 100%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium azide (67 g, 1 mol) was suspended in a mixture of water and acetone (300 mL, 1:1). The mixture was cooled to 0° C., a solution of compound 3 (126.9 g, 0.52 mol) in dry acetone (400 mL) was added at 5° C. The resulting mixture was stirred at 0-5° C. for 4 h and then poured into water (1.5 L). The precipitate was filtered off, washed with water, dried. Additional drying in vacuo over P2O5 gave 4 (130.3 g, 100%)

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. customdried
  4. dry with materialAdditional drying in vacuo over P2O5

Sources & evidence

ORD record
ord-c6836b64572141cab25f5fa4d7bd701f
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

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