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Sodium Azide → 3-azido-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine

HRID 398785
Notes
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Reaction equation

HRID 398785 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH:6]1[C:12](=[O:13])[NH:11][C:10]2[CH:14]=[CH:15][C:16]3[C:21]([C:9]=2[CH2:8][CH2:7]1)=[CH:20][CH:19]=[CH:18][CH:17]=3>CS(C)=O>[N:1]([CH:6]1[C:12](=[O:13])[NH:11][C:10]2[CH:14]=[CH:15][C:16]3[C:21]([C:9]=2[CH2:8][CH2:7]1)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N+:2]=[N-:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 189689123-chloro-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine

Product 1

HCID 189689053-azido-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepineYield 65.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of sodium azide (0.55 g, 8.4 mmol) in DMSO (17 ml) was added 3-chloro-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine (1.6 g, 6.7 mmol) and the suspension was heated at 80° C. for 2.5 h. The hot reaction mixture was added on ice (30 g) and the precipitate was filtered and purified by chromatography on silica gel (200 g) using initially heptane as eluent and subsequently a mixture of heptane and ethyl acetate (1:1) to afford 1.1 g of 3-azido-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine.

Workup

  1. additionThe hot reaction mixture was added on ice (30 g)
  2. filtrationthe precipitate was filtered
  3. custompurified by chromatography on silica gel (200 g)
  4. additionsubsequently a mixture of heptane and ethyl acetate (1:1)

Sources & evidence

ORD record
ord-592d8e403ddf40d9914c4bcd64a64785
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05817654

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes