Water → 5-Azido-3-[3-(trifluoromethoxy)phenyl]-4-thiazolidinone

HRID 724788Notes

Reaction equation

HRID 724788 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH:6]1[S:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=2)[C:7]1=[O:22].O>CN(C=O)C>[N:1]([CH:6]1[S:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=2)[C:7]1=[O:22])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 19710965HCID 19710965, compound

Product 1

HCID 197109685-Azido-3-[3-(trifluoromethoxy)phenyl]-4-thiazolidinoneYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (2.78 g) was added to a solution of 5-chloro-3-(3-trifluoromethoxyphenyl)thiazolidin-4-one (7.50 g) in DMF (50 ml). After 2 hours the mixture was poured into water, extracted with ethyl acetate (x3), dried (MgSO4) and concentrated in vacuo to give the sub-title compound (5.40 g), which was used directly in the next step.

Workup

  1. extractionextracted with ethyl acetate (x3)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71eaaef2a35c4368b7ac6d281bce8344
Source dataset
uspto-grants-1998_01
Patent number
US05705456

Reaction notes

Loading…