Dimethylformamide → HCID 13059344, compound

HRID 2285879Notes

Reaction equation

HRID 2285879 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[CH2:10][CH:11]([C:16]([F:19])([F:18])[F:17])[C:12](=[O:15])[CH2:13]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:21]=[N+:22]=[N-:23].[Na+].CN(C=O)C>CCOCC>[N:21]([CH2:13][C:12](=[O:15])[CH:11]([C:16]([F:19])([F:18])[F:17])[CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:20])=[N+:22]=[N-:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 13059343HCID 13059343, compound

Product 1

HCID 13059344HCID 13059344, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Stir a mixture of 290 mg (0.82 mmol) of the bromo-ketoester of Example 5, 91 mg (1.4 mmol) of NaN3, and 4 ml of dry DMF at 25° C. for 1 hour. Dilute the mixture with ether, wash several times with water and then brine, dry over MgSO4, and remove the solvent in vacuo to give 210 mg of the desired azide (VII, R=CF3, R1,R2 =H, R3 =C6H5CH2) as an oil.

Workup

  1. washwash several times with water
  2. dry with materialbrine, dry over MgSO4
  3. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-08f223efbb3a422798a6425c62d752b1
Source dataset
uspto-grants-1982_04
Patent number
US04325877

Reaction notes

Loading…