Sodium Azide → HCID 25260924, compound

HRID 2246540Notes

Reaction equation

HRID 2246540 reaction equation
Br[CH2:2][CH2:3][CH2:4][Si:5]([CH3:38])([CH3:37])[CH2:6][CH2:7][C:8]1[C:20]2[CH2:19][N:18]3[C:13](=[CH:14][C:15]4[C@@:25]([O:28][C:29](=[O:31])[CH3:30])([CH2:26][CH3:27])[C:24](=[O:32])[O:23][CH2:22][C:16]=4[C:17]3=[O:21])[C:12]=2[N:11]=[C:10]2[CH:33]=[CH:34][CH:35]=[CH:36][C:9]=12.[N-:39]=[N+:40]=[N-:41].[Na+]>CN(C)C=O>[N:39]([CH2:2][CH2:3][CH2:4][Si:5]([CH3:38])([CH3:37])[CH2:6][CH2:7][C:8]1[C:20]2[CH2:19][N:18]3[C:13](=[CH:14][C:15]4[C@@:25]([O:28][C:29](=[O:31])[CH3:30])([CH2:26][CH3:27])[C:24](=[O:32])[O:23][CH2:22][C:16]=4[C:17]3=[O:21])[C:12]=2[N:11]=[C:10]2[CH:33]=[CH:34][CH:35]=[CH:36][C:9]=12)=[N+:40]=[N-:41]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 25260923HCID 25260923, compound

Product 1

HCID 25260924HCID 25260924, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Compound 19 (1.96 g) and sodium azide (725 mg) in N,N-dimethylformamide (15 mL) was heated at 80° C. for 3 hours. The N,N-dimethylformamide was concentrated under reduced pressure and the residue was partitioned between chloroform (25 mL) and 1 N HCl (10 mL). The organic layer was separated, dried and concentrated to obtain the crude product and was purified by eluting on a silica gel column using 1-2% ethanol in dichloromethane to yield 95% of the required product (1.75 g).

Workup

  1. concentrationThe N,N-dimethylformamide was concentrated under reduced pressure
  2. customthe residue was partitioned between chloroform (25 mL) and 1 N HCl (10 mL)
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customto obtain the crude product
  7. customwas purified
  8. washby eluting on a silica gel column

Sources & evidence

ORD record
ord-15ffd71f42b94f43a21b5854b6a82428
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

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