Sodium Azide → HCID 86634012, compound

HRID 1687699Notes

Reaction equation

HRID 1687699 reaction equation
[CH2:1]([N:3]1[C:9](=[O:10])[CH:8](I)[CH2:7][CH2:6][C:5]2[C:12]([O:19][CH3:20])=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:4]1=2)[CH3:2].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O>[N:21]([CH:8]1[C:9](=[O:10])[N:3]([CH2:1][CH3:2])[C:4]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([O:19][CH3:20])[C:5]=2[CH2:6][CH2:7]1)=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 68452177HCID 68452177, compound

Product 1

HCID 86634012HCID 86634012, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combined (+/−)-1-ethyl-3-iodo-6-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (1.3 g), Sodium azide (2.17 g) and N,N-Dimethylformamide (20 mL) in flask under nitrogen and stirred overnight. Partitioned between EtOAc/water. The organic layers were further washed with water, brine, dried (MgSO4), filtered and concentrated. Stripped onto Celite and purified by ISCO chromatography (120 g SiO2, hexane to EtOAc gradient). (+/−)-3-Azido-1-ethyl-6-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one isolated as a clear oil (402 mgs). 1H-NMR (CDCl3, 400 MHz): 7.86 (d, J=8.8 Hz, 1H), 7.13 (d, J=8.8 Hz, 1H), 4.33-4.25 (m, 1H), 3.98 (s, 3H), 3.78-3.71 (broad m, 2H), 3.35-3.23 (broad m, 1H), 2.65-2.35 (broad m, 3H), 1.25-1.21 (m, 3H).

Workup

  1. customPartitioned between EtOAc/water
  2. washThe organic layers were further washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by ISCO chromatography (120 g SiO2, hexane to EtOAc gradient)

Sources & evidence

ORD record
ord-c4dfb9a0549a4a3eaf893973a825eaac
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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