Ethanethiol → HCID 13519521, compound

HRID 371129Notes

Reaction equation

HRID 371129 reaction equation
[H-].[Na+].C(S)C.C[O:7][C:8]1[CH:9]=[C:10]([C:14]23[CH:22]4[CH2:23][CH:19]([CH:20]=[CH:21]4)[CH:18]2[CH2:17][N:16]([CH3:24])[CH2:15]3)[CH:11]=[CH:12][CH:13]=1>CN(C)C=O>[CH3:24][N:16]1[CH2:15][C:14]2([C:10]3[CH:9]=[C:8]([OH:7])[CH:13]=[CH:12][CH:11]=3)[CH:18]([CH:19]3[CH2:23][CH:22]2[CH:21]=[CH:20]3)[CH2:17]1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 20274394HCID 20274394, compound

Product 1

HCID 13519521HCID 13519521, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 733 mg portion of sodium hydride was suspended in 25 ml of dry dimethylformamide and 1.2 ml of ethane thiol in 10 ml of dry dimethylformamide was added dropwise at ice bath temperature. A 1.92 g portion of 2,3,3a,4,7,-7a-hexahydro-3a-(3-methoxyphenyl)-2-methyl-4,7-methano-1H-isoindole was added and the solution was heated at reflux for 6 hours, then cooled and evaporated in vacuo. The residue was taken up in water, extracted with ether, then hexane and neutralized with acetic acid giving a solid which was dissolved in hot methanol and precipitated with ether, then filtered. The filtrate was partially evaporated, then precipitated with ether and hexane. Evaporation of the ether extract gave a foam which was triturated with hexane, giving 240 mg of the desired product as a brown solid, mp 129°-136° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 6 hours
  3. temperaturecooled
  4. customevaporated in vacuo
  5. extractionextracted with ether
  6. dissolutionhexane and neutralized with acetic acid giving a solid which was dissolved in hot methanol
  7. customprecipitated with ether
  8. filtrationfiltered
  9. customThe filtrate was partially evaporated
  10. customprecipitated with ether and hexane
  11. customEvaporation of the ether
  12. extractionextract
  13. customgave a foam which
  14. customwas triturated with hexane

Sources & evidence

ORD record
ord-596253c840714c5bb93837bc230fecba
Source dataset
uspto-grants-1985_07
Patent number
US04529736

Reaction notes

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