Sodium hydride → Ethyl 2-(4-(4-fluoro-2-nitrophenyl-amino)phenoxy)propionate

HRID 1262460Notes

Reaction equation

HRID 1262460 reaction equation
[H-].[Na+].F[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:28]=[CH:27][C:18]([O:19][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=1>CS(C)=O.O>[F:10][C:7]1[CH:8]=[CH:9][C:4]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([O:19][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:27][CH:28]=2)=[C:5]([N+:11]([O-:13])=[O:12])[CH:6]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 677672,5-DifluoronitrobenzeneHCID 11138333Ethyl 2-(4-aminophenoxy)propanoate

Product 1

HCID 13083977Ethyl 2-(4-(4-fluoro-2-nitrophenyl-amino)phenoxy)propionate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2.5 g of sodium hydride paste (60% in mineral oil) was added in portions to a stirred solution of 9.9 g of 2,5-difluoronitrobenzene and 12.7 g of 1E in 200 ml of dimethyl sulfoxide. The resulting mixture was held at 160°-170° C. for 24 hours, then was cooled, diluted with 1000 ml of water and extracted with ether. The extract was chromatographed on silica gel to give ethyl 2-(4-(4-fluoro-2-nitrophenyl-amino)phenoxy)propionate (7A) as a viscous oil.

Workup

  1. temperaturewas cooled
  2. extractionextracted with ether
  3. customThe extract was chromatographed on silica gel

Sources & evidence

ORD record
ord-8f8fbbc00aa54b36a4f7a6d01b39bfa8
Source dataset
uspto-grants-1984_06
Patent number
US04452626

Reaction notes

Loading…