Sodium Azide → HCID 19076175, compound

HRID 965280Notes

Reaction equation

HRID 965280 reaction equation
Cl[CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:17].[N-:18]=[N+:19]=[N-:20].[Na+]>CS(C)=O>[N:18]([CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:17])=[N+:19]=[N-:20]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 19076181HCID 19076181, compound

Product 1

HCID 19076175HCID 19076175, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 3-chloro-7-carbomethoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 4 (3.50 g, 13.8 mmol) and NaN3 (1.08 g, 16.6 mmol) in DMSO (100 mL) was stirred at RT for 22 h, then heated at 75° C. for an additional 2 h. The resulting solution was poured into ice water (500 mL) and the resulting precipitate was filtered and dried under vacuum to give 5 (3.26 g, 91%). 1H NMR (250 MHz, CDCl3) δ 8.09 (1H, brs, H-1), 7.93 (2H, m, H-6,8), 7.10 (1H, d, j=6.5 Hz, H-9), 3.93 (3H, s, OCH3), 3.88 (1H, dd, j=8.0, 11.5 Hz, H-3), 3.01 (1H, ddd, j=8.0, 13.5, 13.5 Hz, H-5), 2.82 (1H, m, H-5), 2.59 (1H, m, H-4), 2.36 (1H , H-4).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-be93a8e843d749ba8fea0b25163a842e
Source dataset
uspto-grants-1998_06
Patent number
US05773512

Reaction notes

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