p-Toluenesulfonic acid → 2-(2,3-Dihydrobenzofuran-5-yl)-1-morpholinoethanethione

HRID 868619Notes

Reaction equation

HRID 868619 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]([C:10]1[CH:11]=[CH:12][C:13]2[O:17][CH2:16][CH2:15][C:14]=2[CH:18]=1)(=O)[CH3:8].[S].C1(C)C=CC([S:26](O)(=O)=O)=CC=1>CO>[O:17]1[C:13]2[CH:12]=[CH:11][C:10]([CH2:7][C:8]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[S:26])=[CH:18][C:14]=2[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 1452201-(2,3-Dihydro-5-benzofuranyl)ethanoneHCID 5362487Sulfur

Product 1

HCID 137043802-(2,3-Dihydrobenzofuran-5-yl)-1-morpholinoethanethione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Morpholine (1.5 ml), 2,3-dihydro-5-acetylbenzofuran (2.0 g), sulfur (0.395 g) and p-toluene sulfonic acid (0.060 g) were heated at reflux. After 3 hours, the reaction mixture was cooled and 6 ml of methanol added. This solution was further cooled which precipitated the morpholide. The precipitate was filtered and washed with cold methanol to give 2,3-dihydrobenzofuran-5-ylthioacetic acid morpholide, m.p.--144°-147° C.

Workup

  1. temperatureat reflux
  2. temperaturethe reaction mixture was cooled
  3. temperatureThis solution was further cooled which
  4. customprecipitated the morpholide
  5. filtrationThe precipitate was filtered
  6. washwashed with cold methanol

Sources & evidence

ORD record
ord-9d3301cc607748479d10fed339056f31
Source dataset
uspto-grants-1988_10
Patent number
US04780480

Reaction notes

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