Sodium Azide → HCID 19022644, compound

HRID 1034452Notes

Reaction equation

HRID 1034452 reaction equation
I[CH:2]1[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH2:7][C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[NH:4][C:3]1=[O:21].[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:22]([CH:2]1[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH2:7][C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[NH:4][C:3]1=[O:21])=[N+:23]=[N-:24]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 19022650HCID 19022650, compound

Product 1

HCID 19022644HCID 19022644, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2,3,4,5-tetrahydro-3-iodo-4-(4-methoxyphenyl)-1H-1-benzazepin-2-one (270 mg, 0.687 mmol) in 2mL of dimethylformamide was treated with sodium azide (65 mg, 1.0 mmol, 1.5eq) and the mixture was heated at 60° C. in an oil bath for 14 hours. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried (MgSO4) and filtered. Removal of the solvent under vacuum followed by column chromatography on silica gel (eluant 2:1; hexane/ethyl acetate) gave 148 mg (70%) of the product as a single isomer. 1H NMR (400 MHz, CDCl3): 295 (dd; 7,14 Hz; 1H), 3.15 (dd; 13, 14 Hz; 1H), 3.75 (m, 1H), 3.80 (s, 3H), 4.11 (d, 7Hz, 1H), 6.89 (d, 8Hz, 2H), 7.04 (d, 8Hz, 1 H), 7.20-7.30 (m, 5H), 7.88 (br s, 1H). FAB-MS: calculated for C17H16N4O2 308; found 309 (40%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customRemoval of the solvent under vacuum

Sources & evidence

ORD record
ord-111672fdd15a4e7483c2f1ce1d8005cd
Source dataset
uspto-grants-1994_05
Patent number
US05317017

Reaction notes

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