Water → HCID 23369652, compound

HRID 1900828Notes

Reaction equation

HRID 1900828 reaction equation
Br[CH2:2][CH:3]1[O:18][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]1[CH3:19])[NH:11][C:10](=[O:16])[C:9]([CH3:17])=[CH:8]3.[N-:20]=[N+:21]=[N-:22].[Na+].C(OCC)(=O)C.O>CN(C)C=O>[N:20]([CH2:2][CH:3]1[O:18][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]1[CH3:19])[NH:11][C:10](=[O:16])[C:9]([CH3:17])=[CH:8]3)=[N+:21]=[N-:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 23369678HCID 23369678, compound

Product 1

HCID 23369652HCID 23369652, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

The compound obtained in Example 295 (1.49 g, 4.62 mmol) was dissolved in dimethyformamide (20 ml). Sodium azide (1.8 g, 27.69 mmol) was added to the mixture, and stirred at 150° C. for 3 hours. After cooling, ethyl acetate and water were added to the mixture for phase separation. The organic phase was washed with water and saturated aqueous NaCl solution in this order, and dried. The solvent was distilled off under reduced pressure to obtain 1.43 g (assayed quantitatively) of the title compound as crude crystals.

Workup

  1. temperatureAfter cooling
  2. washThe organic phase was washed with water and saturated aqueous NaCl solution in this order
  3. customdried
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-534302b78aff4fa8866235119af46238
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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