Sodium Azide → HCID 86591159, compound

HRID 860796Notes

Reaction equation

HRID 860796 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[O:16][CH2:15][CH2:14][O:13]2)=[CH:8][C:7]=1[C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:4].[N-:32]=[N+:33]=[N-:34].[Na+]>CO>[N:32]([CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[O:16][CH2:15][CH2:14][O:13]2)=[CH:8][C:7]=1[C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:4])=[N+:33]=[N-:34]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 69021146HCID 69021146, compound

Product 1

HCID 86591159HCID 86591159, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of intermediate (25) (0.105 mol) and sodium azide (6.84 g) in methanol (160 ml) was stirred and refluxed for 6 h. The mixture was cooled, poured into ice water and extracted with DCM. The organic layer was dried (MgSO4), filtered off and evaporated till dryness. The product was used without further purification, yielding 2-azido-N-[2-benzoyl-4-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]phenyl]acetamide (intermediate 26).

Workup

  1. temperaturerefluxed for 6 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered off
  6. customevaporated till dryness
  7. customThe product was used without further purification

Sources & evidence

ORD record
ord-77cf3cafdc894a0eb3c3be4deeb2923e
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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