Acetone → 3-(2-Chlorobenzoyl)-2-(2-nitroethenylamino)-5-ethylthiophene

HRID 1885200Notes

Reaction equation

HRID 1885200 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:16][CH3:17])=[CH:5][C:6]=1[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14].O1CCN([CH:24]=[CH:25][N+:26]([O-:28])=[O:27])CC1.Cl.CC(C)=O>O>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]([C:6]1[CH:5]=[C:4]([CH2:16][CH3:17])[S:3][C:2]=1[NH:1][CH:24]=[CH:25][N+:26]([O-:28])=[O:27])=[O:15]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 683970Morpholine, 4-(2-nitroethenyl)-HCID 13163365(2-Amino-5-ethylthiophen-3-yl)(2-chlorophenyl)methanone

Product 1

HCID 677573983-(2-Chlorobenzoyl)-2-(2-nitroethenylamino)-5-ethylthiopheneYield 84.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-amino-3-(2-chlorobenzoyl)-5-ethylthiophene (5.30 g), 1-morpholino-2-nitroethene (3.16 g), 6N HCl (5 ml) and acetone (25 ml) was stirred at room temperature for one hour. Water was added to the mixture, which was extracted with ethene acetate. The extract was washed with water and dried over MgSO4, and then the solvent was distilled off to obtain 3-(2-chlorobenzoyl)-2-(2-nitroethenylamino)-5-ethylthiophene as crystals (5.65 g, 84.1%). The crystals were recrystallized from acetone to obtain yellow plates, mp: 125°-126° C.

Workup

  1. extractionwas extracted with ethene acetate
  2. washThe extract was washed with water
  3. dry with materialdried over MgSO4
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-ade5c1c431d24bb0a7868c1e3253d28c
Source dataset
uspto-grants-1992_09
Patent number
US05143919

Reaction notes

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