Sodium Azide → HCID 11037520, compound

HRID 1516765Notes

Reaction equation

HRID 1516765 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([O:17][CH2:18][CH2:19][O:20][CH2:21][N:22]1[CH:29]=[C:28]([CH:30]=[CH2:31])[C:26](=[O:27])[NH:25][C:23]1=[O:24])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N-:32]=[N+:33]=[N-:34].[Na+]>COCCOC.O>[C:9]([O:17][CH2:18][CH2:19][O:20][CH2:21][N:22]1[CH:29]=[C:28]([CH:30]([N:32]=[N+:33]=[N-:34])[CH2:31][Br:1])[C:26](=[O:27])[NH:25][C:23]1=[O:24])(=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 67184N-bromobutanimideHCID 11758893HCID 11758893, compound

Product 1

HCID 11037520HCID 11037520, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

N-Bromosuccinimide (NBS, 350 mg, 1.96 mmol) was added in aliquots to a precooled (−5° C.) suspension prepared by mixing a solution of 3 (61 mg, 1.95 mmol) in 1,2-dimethoxyethane (25 ml) with a solution of sodium azide (510 mg, 7.84 mmol) in water (1.2 ml). The initial yellow color faded away after each addition. When all the NBS was consumed, the reaction mixture was allowed to stand at 0° C. for 30 min., prior to pouring onto ice-water (25 ml), and extraction with dichloromethane (3×50 ml). The dichloromethane extract was washed with cold water (25 ml), dried (Na2SO4), the solvent was removed in vacuo to yield a residue which was purified by elution from a silica gel column using chloroform:methanol (98:2, v/v) as eluent to yield 4 (388 mg, 45.5%) as a viscous oil which was used in the next reaction.

Workup

  1. customprepared
  2. additionafter each addition
  3. customWhen all the NBS was consumed
  4. additionto pouring onto ice-water (25 ml), and extraction with dichloromethane (3×50 ml)
  5. extractionThe dichloromethane extract
  6. washwas washed with cold water (25 ml)
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was removed in vacuo
  9. customto yield a residue which
  10. customwas purified by elution from a silica gel column

Sources & evidence

ORD record
ord-4bc87c2b75c04092a23af1f51ab89069
Source dataset
uspto-grants-2012_07
Patent number
US08227594B2

Reaction notes

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