Benzene → 4-(Pyrrolidin-1-yl)-1-benzothiopyran-1,1(2H)-dione

HRID 435998Notes

Reaction equation

HRID 435998 reaction equation
[S:1]1(=[O:13])(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3][CH2:2]1.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C1C=CC=CC=1>O>[N:14]1([C:4]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[S:1](=[O:13])(=[O:12])[CH2:2][CH:3]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 31268PyrrolidineHCID 3459512,3-Dihydro-1-benzothiopyran-1,1,4-trione

Product 1

HCID 214134244-(Pyrrolidin-1-yl)-1-benzothiopyran-1,1(2H)-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.8 g. (0.05 mole) of thiochroman-4-one 1,1-dioxide, 5.3 g. (0.075 mole) of pyrrolidine, and 150 ml. of benzene was placed in a flask equipped with a Dean-Stark water separator and was refluxed for 4 hr. The precipitate (4.9 g.) which separated on standing at room temperature was collected. Concentration to one-fourth the original volume gave an additional 5.0 g. These crops were combined and recrystallized from benzene to give 8.0 g. of product, m.p. 154°-157° dec.

Workup

  1. additionA mixture of 9.8 g
  2. temperaturewas refluxed for 4 hr
  3. customThe precipitate (4.9 g.) which separated
  4. customon standing at room temperature
  5. customwas collected
  6. concentrationConcentration to one-fourth the original volume
  7. customgave an additional 5.0 g
  8. customrecrystallized from benzene
  9. customto give 8.0 g

Sources & evidence

ORD record
ord-14338c444e494259bd485ec0ee6dc1c6
Source dataset
uspto-grants-1977_02
Patent number
US04007203

Reaction notes

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