Chloroform → N-Methyl-(7-isopropoxycarbonyl-6-methyl-2,3-dihydropyrrolo-[2,1-b]thiazol-3-ylidene)acetamide

HRID 2372383Notes

Reaction equation

HRID 2372383 reaction equation
[CH3:1][NH:2][C:3](=[O:20])[CH:4]=[C:5]1[CH2:9][S:8][C:7]2=[C:10]([C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])[CH:11]([CH3:13])[CH2:12][N:6]12.C(Cl)(Cl)Cl.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(=O)([O-])O.[Na+]>O.O1CCCC1>[CH3:1][NH:2][C:3](=[O:20])[CH:4]=[C:5]1[CH2:9][S:8][C:7]2=[C:10]([C:14]([O:16][CH:17]([CH3:18])[CH3:19])=[O:15])[C:11]([CH3:13])=[CH:12][N:6]12

Participants

7

Reactant 4

HCID 6212ChloroformHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 67755339HCID 67755339, compound

Product 1

HCID 49824961N-Methyl-(7-isopropoxycarbonyl-6-methyl-2,3-dihydropyrrolo-[2,1-b]thiazol-3-ylidene)acetamideYield 82.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

15.3 g of N-methyl-(7-isopropoxycarbonyl-6-methyl-2,3,5,6-tetrahydropyrrolo[2,1-b]thiazol-3-ylidene)acetamide was dissolved in a solvent mixture comprising 300 ml of chloroform and 120 ml of tetrahydrofuran. Then 11.7 g of 2,3-dichloro-5,6-dicyano-parabenzoquinone was added thereto under stirring and cooling with cold water. After 0.5 hour, a saturated aqueous solution of sodium hydrogencarbonate was added thereto. After stirring, the insoluble matters were filtered off with the use of celite and the filtrate was extracted with chloroform. The chloroform phase was washed with water and a saturated aqueous solution of sodium chloride and dried. After distilling off the solvent, the obtained crude crystals were recrystallized from ethanol. Thus 12.5 g of the title compound was obtained.

Workup

  1. stirringAfter stirring
  2. filtrationthe insoluble matters were filtered off with the use of celite
  3. extractionthe filtrate was extracted with chloroform
  4. washThe chloroform phase was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride and dried
  6. distillationAfter distilling off the solvent
  7. customthe obtained crude crystals
  8. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-30b34b19d7064fe8b6b56eb6b717cb26
Source dataset
uspto-grants-1992_03
Patent number
US05098919

Reaction notes

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