Ethanol → HCID 19972667, compound

HRID 2259872Notes

Reaction equation

HRID 2259872 reaction equation
Cl[CH2:2][C:3]1[C:12]2[O:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:9]([CH3:19])[C:8](=[O:20])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[N-:21]=[N+:22]=[N-:23].[Na+].O.C(O)C>CN(C)C=O>[N:21]([CH2:2][C:3]1[C:12]2[O:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:9]([CH3:19])[C:8](=[O:20])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[N+:22]=[N-:23]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 33557Sodium AzideHCID 19972408HCID 19972408, compound

Product 1

HCID 19972667HCID 19972667, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 22.8 g of Intermediate XIX and 6.8 g of sodium azide in 110 ml of dimethylformamide was stirred for 3 hours at 100° C. After cooling to ambient temperature, 130 ml of water and 88 ml of ethanol were added to the reaction mixture. After 1 hour, the crystals were collected by vacuum filtration, washed with water, and desiccated. Yield: 22 g of the title product. A sample recrystallized from ethanol had a melting point of 132°-134° C.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. waitAfter 1 hour
  3. filtrationthe crystals were collected by vacuum filtration
  4. washwashed with water
  5. customA sample recrystallized from ethanol

Sources & evidence

ORD record
ord-ef408547087f42758fd5ae197bffd934
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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