Water → 3-(2,6-Dichloroanilino)-2-thiophenglyoxylic acid ethyl ester

HRID 1680161Notes

Reaction equation

HRID 1680161 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:3]=1[NH:4][C:5]1[CH:9]=[CH:8][S:7][CH:6]=1.C(N(CC)CC)C.[CH2:22]([O:24][C:25](=[O:29])[C:26](Cl)=[O:27])[CH3:23].O>O1CCCC1.C(OCC)(=O)C>[CH2:22]([O:24][C:25](=[O:29])[C:26]([C:6]1[S:7][CH:8]=[CH:9][C:5]=1[NH:4][C:3]1[C:10]([Cl:14])=[CH:11][CH:12]=[CH:13][C:2]=1[Cl:1])=[O:27])[CH3:23]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 234572233-(2,6-Dichloroanilino)thiophen

Product 1

HCID 705760593-(2,6-Dichloroanilino)-2-thiophenglyoxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.44 g (10 mmoles) of 3-(2,6-dichloroanilino)thiophen, 1.01 g of triethylamine and 1.37 g (10 mmoles) of chlorooxalic acid ethyl ester are stirred in 20 ml of tetrahydrofuran at room temperature for 10 hours. 100 ml each of water and ethyl acetate are added, and the organic phase is dried and concentrated. Recrystallization of the residue from ethanol gives 3-(2,6-dichloroanilino)-2-thiophenglyoxylic acid ethyl ester.

Workup

  1. customthe organic phase is dried
  2. concentrationconcentrated
  3. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-82acdef777024c0cbb806856f3439b3d
Source dataset
uspto-grants-1981_06
Patent number
US04272507

Reaction notes

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