Dimethyl Sulfide → HCID 15132167, compound

HRID 982310Notes

Reaction equation

HRID 982310 reaction equation
S(C)C.[CH:4]([NH:6][C:7]1[C:8]([Cl:25])=[CH:9][C:10]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][C@H:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11]=2[CH:24]=1)=O>C1COCC1>[CH3:4][NH:6][C:7]1[C:8]([Cl:25])=[CH:9][C:10]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][C@H:12]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:11]=2[CH:24]=1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 15132166HCID 15132166, compound

Product 1

HCID 15132167HCID 15132167, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Me2S in THF (13.25 ml) was added dropwise to the product obtained in Example III (2.55 g, 0.008 mol) dissolved in 30 ml of THF with stirring and cooling in an ice bath. The ice bath was removed and the mixture was heated to reflux for 3.5 hours. The mixture was left to stand at room temperature overnight. Ethanolic HCl was added dropwise to the mixture with cooling (ice bath) and stirring until a pH of 1.5 was reached. The mixture was heated to reflux for one hour and then the solvent was removed. The residue was stirred with ether and 1N NaOH. The dried ether solution was evaporated in vacuo. The residue was crystallized from isopropyl ether, m.p. 98°-100° C. [α]26D +67.3 (DMF, c=1).

Workup

  1. temperaturecooling in an ice bath
  2. customThe ice bath was removed
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 3.5 hours
  5. waitThe mixture was left
  6. additionEthanolic HCl was added dropwise to the mixture
  7. temperaturewith cooling (ice bath)
  8. stirringstirring until a pH of 1.5
  9. temperatureThe mixture was heated
  10. temperatureto reflux for one hour
  11. customthe solvent was removed
  12. stirringThe residue was stirred with ether and 1N NaOH
  13. customThe dried ether solution was evaporated in vacuo
  14. customThe residue was crystallized from isopropyl ether, m.p. 98°-100° C. [α]26D +67.3 (DMF, c=1)

Sources & evidence

ORD record
ord-405bc55f5ab24d22a4df7265c7aa1211
Source dataset
uspto-grants-1991_02
Patent number
US04996202

Reaction notes

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