Water → Eltenac

HRID 1680149Notes

Reaction equation

HRID 1680149 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:3]=1[NH:4][C:5]1[C:6]([CH2:10][C:11]#N)=[CH:7][S:8][CH:9]=1.[OH-:18].[Na+].[OH2:20]>CO>[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:3]=1[NH:4][C:5]1[C:6]([CH2:10][C:11]([OH:20])=[O:18])=[CH:7][S:8][CH:9]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 23457191HCID 23457191, compound

Product 1

HCID 51717Eltenac

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

31 g (0.11 mole) of 4-(2,6-dichloroanilino)-3-thiophenacetonitrile are boiled in a solution of 110 g of sodium hydroxide in 450 ml of water and 220 ml of methanol for 4 hours. The mixture is diluted with 2 liters of warm water and extracted with toluene, the aqueous phase is acidified and the precipitate of 4-(2,6-dichloroanilino)-3-thiophenacetic acid, which has formed, is filtered off. The precipitate is boiled up with diisopropyl ether and dried; it then melts at 179° to 180°.

Workup

  1. extractionextracted with toluene

Sources & evidence

ORD record
ord-11994670a21d4a459082f1761c6995ac
Source dataset
uspto-grants-1981_06
Patent number
US04272507

Reaction notes

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