Hydrochloric Acid → HCID 14796240, compound

HRID 1032230Notes

Reaction equation

HRID 1032230 reaction equation
[Na].[SH:2][C:3]1[S:4][CH2:5][CH2:6][N:7]=1.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:16]([NH:18][C:19](=[O:21])[CH:20]=1)=[O:17].Cl>O1CCCC1>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]1[CH:20]([S:2][C:3]2[S:4][CH2:5][CH2:6][N:7]=2)[C:19](=[O:21])[NH:18][C:16]1=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21924318HCID 21924318, compoundHCID 178527882HCID 178527882, compound

Product 1

HCID 14796240HCID 14796240, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of mercaptothiazoline sodium (4.50 g) in tetrahydrofuran (30 ml) is added to a refluxed solution of 2-(2-chlorophenyl)maleimide (3.00 g) in tetrahydrofuran (40 ml) and the mixture is refluxed for 10 minutes. After cooling, the reaction mixture is diluted using diluted hydrochloric acid and the solvent is distilled off. The residue is extracted with ethyl acetate and the extract is washed with water and dried over magnesium sulfate. The ethyl acetate is distilled off and the residue is subjected to silica gel chromatography, elution being carried out with dichloromethanemethanol (50:1). The eluate is recrystallized from ethanol to give 2-(2-chlorophenyl)-3-(2-thiazolin-2-ylthio)succinimide (1.40 g), m.p. 195°-200° C.

Workup

  1. temperaturethe mixture is refluxed for 10 minutes
  2. temperatureAfter cooling
  3. additionthe reaction mixture is diluted
  4. distillationthe solvent is distilled off
  5. extractionThe residue is extracted with ethyl acetate
  6. washthe extract is washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationThe ethyl acetate is distilled off
  9. washthe residue is subjected to silica gel chromatography, elution
  10. customThe eluate is recrystallized from ethanol

Sources & evidence

ORD record
ord-0240411d54a44f4cb4e5c4edd87a3f6b
Source dataset
uspto-grants-1990_09
Patent number
US04957537

Reaction notes

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