Sodium metaborate → HCID 70575286, compound

HRID 1680158Notes

Reaction equation

HRID 1680158 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:20])=O)[CH3:2].B([O-])=O.[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:20])[CH3:2]

Participants

4

Reactant 2

HCID 145326Sodium metaborateHCID 70574207HCID 70574207, compound

Product 1

HCID 70575286HCID 70575286, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.32 g (1 mmole) of 3-(2-chloro-6-methylanilino)-2-thiophenglyoxylic acid ethyl ester and 1 g of sodium boranate are warmed to 80° in 10 ml of dimethylformamide for 2 hours. The mixture is then poured onto water and washed with diethyl ether, and the aqueous phase is acidified and extracted with ethyl acetate. Concentration of the organic phase and column chromatography (silica gel/methylene chloride) give, in the first fraction, 3-(2-chloro-6-methylanilino)-2-thiophenacetic acid ethyl ester.

Workup

  1. additionThe mixture is then poured onto water
  2. washwashed with diethyl ether
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-96d01c276ff2437d969da20f26133ecb
Source dataset
uspto-grants-1981_06
Patent number
US04272507

Reaction notes

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