Sodium Methoxide → HCID 14154795, compound

HRID 2291834Notes

Reaction equation

HRID 2291834 reaction equation
C[O-].[Na+].C(O)(=O)C.[CH3:8][N:9]([CH3:20])[C@@H:10]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11][SH:12]>CO>[CH3:20][N:9]([CH3:8])[C@@H:10]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11][SH:12]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86742677HCID 86742677, compound

Product 1

HCID 14154795HCID 14154795, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methylate (0.2 g) is added under an atmosphere of nitrogen to (S)-2-dimethylamino-3-phenylpropanethiol acetate (crude; 20 g) dissolved in methanol (50 cc), and the mixture is heated under reflux for 2 hours. The mixture is then concentrated to dryness under reduced pressure (2.7 kPa) at 30° C. to give a liquid which is purified by distillation. (S)-2-Dimethylamino-3-phenylpropanethiol (2.4 g) is obtained in the form of a colourless liquid [b.p. (14 Pa)=95° C.], which is used as it is in the following reaction.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe mixture is then concentrated to dryness under reduced pressure (2.7 kPa) at 30° C.
  4. customto give a liquid which
  5. distillationis purified by distillation

Sources & evidence

ORD record
ord-7cea9ab1f3e84a679a4dc2671229ac2d
Source dataset
uspto-grants-1989_01
Patent number
US04798827

Reaction notes

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