Phosphorus pentachloride → N-(2,6-dichlorophenyl)-2,3-dihydro-2-oxothieno[3,4-b]pyrrole

HRID 1680171Notes

Reaction equation

HRID 1680171 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:3]=1[NH:4][C:5]1[C:6]([CH2:10][C:11](O)=[O:12])=[CH:7][S:8][CH:9]=1.P(Cl)(Cl)(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:3]=1[N:4]1[C:11](=[O:12])[CH2:10][C:6]2=[CH:7][S:8][CH:9]=[C:5]12

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 51717Eltenac

Product 1

HCID 23457240N-(2,6-dichlorophenyl)-2,3-dihydro-2-oxothieno[3,4-b]pyrrole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1 g (0.33 mmole) of 4-(2,6-dichloroanilino)-3-thiophenacetic acid and 0.7 g (0.33 mmole) of phosphorus pentachloride are stirred in 10 ml of toluene at room temperature for half an hour. The mixture is extracted with water and sodium bicarbonate solution, clarified with bleaching earth (for example Tonsil®) and concentrated. Recrystallization of the residue from isopropanol yields N-(2,6-dichlorophenyl)-2,3-dihydro-2-oxothieno[3,4-b]pyrrole (m. 187° to 188°).

Workup

  1. extractionThe mixture is extracted with water and sodium bicarbonate solution
  2. concentrationconcentrated
  3. customRecrystallization of the residue from isopropanol

Sources & evidence

ORD record
ord-142fa22fbd3b4f498e995f2f7de0a3d6
Source dataset
uspto-grants-1981_06
Patent number
US04272507

Reaction notes

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