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

HRID 398789
Notes
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Reaction equation

HRID 398789 reaction equation
Cl[CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][C:12]3[C:17]([C:5]=2[CH2:4][CH2:3]1)=[CH:16][CH:15]=[CH:14][CH:13]=3.[N-:18]=[N+:19]=[N-:20].[Na+].O>CS(C)=O>[N:18]([CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][C:12]3[C:17]([C:5]=2[CH2:4][CH2:3]1)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N+:19]=[N-:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 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]azepine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 3-chloro-4-oxo-2,3,4,5-tetrahydro-1H- naphtho-[2,1-b]azepine (16.6 g, 67.6 mmol) in DMSO (80 ml) was added sodium azide (8.8 g, 135 mmol) and the suspension was heated at 60° C. for 5 h. The hot reaction mixture was poured into water (1 L). The precipitate was isolated by filtration and washed with water. After drying in vacuo 16.3 g of 3-azido-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine was obtained.

Workup

  1. customThe precipitate was isolated by filtration
  2. washwashed with water
  3. dry with materialAfter drying in vacuo 16.3 g of 3-azido-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine
  4. customwas obtained

Sources & evidence

ORD record
ord-f98ab990fc334b28bba6451aa25b50e3
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