Sodium Azide → HCID 19025473, compound

HRID 1033403Notes

Reaction equation

HRID 1033403 reaction equation
I[CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:15].[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O>[N:16]([CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:15])=[N+:17]=[N-:18]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 19025624HCID 19025624, compound

Product 1

HCID 19025473HCID 19025473, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Iodo-7-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (4.074 g, 12.85 mmol) and sodium azide (4.178 g, 64.3 mmol, 5 eq.) were dissolved in 50 mL of dimethylformamide and heated with stirring at 60° for 2 hours. The solvent was evaporated under vacuum at room temperature and the residue redissolved in 150 mL of ethyl acetate and washed with water (3×50 mL) and brine (1×50 mL). The organic layer was separated, dried over MgSO4, filtered and evaporated to dryness under vacuum to yield 2.538 g (10.94 mmol, 85%) of product. 1H NMR (200 MHz, CDCl3): 2.2-2.7 (m,3H), 2.90 (m,1H), 3.75 (s,3H), 3.80 (m,1H), 6.75 (m,2H), 6.95 (d,8 Hz, 2H), 8.22 (br s,1H). FAB-MS: calculated for C11H12N4O2 232; found 233 (M+H,30%).

Workup

  1. temperatureheated
  2. customThe solvent was evaporated under vacuum at room temperature
  3. dissolutionthe residue redissolved in 150 mL of ethyl acetate
  4. washwashed with water (3×50 mL) and brine (1×50 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-b6709843630a4b7a9e85cadc33204e60
Source dataset
uspto-grants-1994_05
Patent number
US05310737

Reaction notes

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