Water → HCID 19972552, compound

HRID 2259860Notes

Reaction equation

HRID 2259860 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[C:14]2[O:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([CH3:21])[C:10](=[O:22])[C:9]=2[CH:8]=[CH:7][CH:6]=1.[N-:23]=[N+:24]=[N-:25].[Na+].O>CN(C)C=O>[N:23]([CH2:2][CH2:3][O:4][C:5]1[C:14]2[O:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([CH3:21])[C:10](=[O:22])[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[N+:24]=[N-:25]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 19972646HCID 19972646, compound

Product 1

HCID 19972552HCID 19972552, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 15.2 g of Intermediate XI and 6.24 g of sodium azide in 150 ml of anhydrous dimethylformamide was stirred at 70°-75° C. for 12 hours. After cooling to 20°-25° C., the reaction mixture was poured into 1.5 liters of water and extracted with dichloromethane. The organic solution was washed with aqueous sodium chloride solution and dried on anhydrous sodium sulfate. The solvents were evaporated off in vacuo. The residue was taken up in water, collected by suction filtration and dried to give 14 g of the title compound, m.p. 119°-120° C.

Workup

  1. temperatureAfter cooling to 20°-25° C.
  2. extractionextracted with dichloromethane
  3. washThe organic solution was washed with aqueous sodium chloride solution
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvents were evaporated off in vacuo
  6. filtrationcollected by suction filtration
  7. customdried

Sources & evidence

ORD record
ord-f95fb348299542019184b6c55a076907
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

Loading…