Water → HCID 12756953, compound

HRID 1389285Notes

Reaction equation

HRID 1389285 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([S:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[CH:3]=1.O.[OH-].[Na+]>C(O)(=O)C.[Fe]>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([S:12][C:4]2[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=2[CH2:8][C:9]([OH:11])=[O:10])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 12756952HCID 12756952, compound

Product 1

HCID 12756953HCID 12756953, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 19 g [4-fluoro-2-(4-nitrophenylthio)phenyl] acetic acid in 60 ml of acetic acid was slowly added dropwise into a boiling mixture of 300 ml water and 30 g iron powder. The mixture was then stirred and refluxed for 6 hours. After cooling, 200 ml of a 20% sodium hydroxide solution were added, the solution filtered and the filtrate acidified with acetic acid. After standing overnight, the separated product was filtered, washed with a small quantity of water and dried in vacuo. There were obtained 9.5 g of crude [2-(4-aminophenylthio)-4-fluorophenyl]acetic acid melting at 151°-155° C. After a single crystallization from a mixture of benzene and petroleum ether, the product was pure and melted at 154°-156° C.

Workup

  1. temperaturerefluxed for 6 hours
  2. temperatureAfter cooling
  3. filtrationthe solution filtered
  4. filtrationthe separated product was filtered
  5. washwashed with a small quantity of water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-0845bfcbcb2647258db46ecac52da003
Source dataset
uspto-grants-1981_01
Patent number
US04243805

Reaction notes

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