Water → Methyl 2-[p-(5-acetamido-4-fluoro-2-nitroanilino)phenoxy]propionate

HRID 259739Notes

Reaction equation

HRID 259739 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9](F)=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6].[NH2:16][C:17]1[CH:29]=[CH:28][C:20]([O:21][CH:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=1.O>O1CCOCC1.C(OCC)C>[C:5]([NH:4][C:3]1[C:2]([F:1])=[CH:11][C:10]([N+:12]([O-:14])=[O:13])=[C:9]([CH:8]=1)[NH:16][C:17]1[CH:18]=[CH:19][C:20]([O:21][CH:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24])=[CH:28][CH:29]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 3

HCID 962WaterHCID 14624893N-(2,5-Difluoro-4-nitrophenyl)acetamideHCID 22060471Methyl 2-(4-aminophenoxy)propanoate

Product 1

HCID 19430914Methyl 2-[p-(5-acetamido-4-fluoro-2-nitroanilino)phenoxy]propionate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2',5'-difluoro-4'-nitroacetanilide (7.35 g, 0.034 mol) and methyl 2-(4-aminophenoxy) -propionate (16.6 g, 0.085 mol) in dioxane is refluxed for 2 days, cooled to room temperature and poured into water. The resultant aqueous mixture is extracted with ethyl acetate and the organic extracts are combined, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a dark red gum. The gum is dissolved in hot diethyl ether and, after stirring briefly, an orange solid forms. The solid is collected via filtration and dried to give the title product as an orange solid, mp 126.5°-128.4° C.

Workup

  1. temperatureis refluxed for 2 days
  2. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a dark red gum
  7. filtrationThe solid is collected via filtration
  8. customdried

Sources & evidence

ORD record
ord-a7bc7c77a9b64c098331976cca0cef57
Source dataset
uspto-grants-1996_06
Patent number
US05523277

Reaction notes

Loading…