Hydrochloric Acid → 3-(Benzothiazol-2-yl)-4-Phenyl-2-(5H) Furanone

HRID 327757

Reaction equation

HRID 327757 reaction equation
[C:1]([O:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=O)(=[O:3])[CH3:2].[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1CC([O-])=O.[OH-].[Na+].Cl>CO>[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[C:2]1[C:1](=[O:3])[O:4][CH2:5][C:6]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 222851Ethanone, 2-(acetyloxy)-1-phenyl-HCID 7128533alpha-(Benzothiazol-2-yl)-acetate

Product 1

HCID 541813413-(Benzothiazol-2-yl)-4-Phenyl-2-(5H) Furanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-acetoxyacetophenone (from Example 1) (8.9 g, 0.05M) and α-(benzothiazol-2-yl)-acetate (from Example 3) dissolved in methanol (40 mL) by stirring at room temperature was treated at room temperature with a solution prepared by dissolving sodium hydroxide pellets (2.5 g) in methanol (30 mL) by stirring. A slight exothermic reaction was observed. After being stirred at about room temperature for about 1.0 hour, the reaction mixture was acidified to a pH of about 4 by the dropwise addition of concentrated HCl. The product which was a dark brown colored semi-crystalline mass was washed by decantation and dried in air (yield--12.0 g (81.9% of the theoretical yield). Mass spectrometry indicated that the product largely consisted of the following desired compound: ##STR16##

Workup

  1. additionwas treated at room temperature with a solution
  2. customprepared
  3. stirringby stirring
  4. customA slight exothermic reaction
  5. stirringAfter being stirred at about room temperature for about 1.0 hour
  6. washwas washed by decantation
  7. customdried in air (
  8. customyield--12.0 g (81.9% of the
  9. customtheoretical yield)

Sources & evidence

ORD record
ord-6a524c00b0354527b91f0643f335c8bc
Source dataset
uspto-grants-1993_12
Patent number
US05274072

Linked notes

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