Methanol → O,O-Diethyl S-[(2-methylpropane-2-sulfinyl)methyl] phosphorothioate

HRID 1578904Notes

Reaction equation

HRID 1578904 reaction equation
I([O-])(=O)(=O)=O.[Na+].[OH2:7].[P:8](=[O:22])([S:15][CH2:16][S:17][C:18]([CH3:21])([CH3:20])[CH3:19])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11].CO>C(Cl)Cl>[P:8](=[O:22])([S:15][CH2:16][S:17]([C:18]([CH3:20])([CH3:19])[CH3:21])=[O:7])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 13084212Terbufos oxonHCID 23667635Sodium periodate

Product 1

HCID 92037O,O-Diethyl S-[(2-methylpropane-2-sulfinyl)methyl] phosphorothioate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of sodium periodate (11.8 grams, 0.055 mole, 10% excess) in 115 ml. of water, cooled to 0° to 5°C., is added O,O-diethyl S-(tert-butylthio)methyl phosphorothioate (13.6 grams, 0.050 mole) and 5.0 ml. of methanol. The reaction mixture, in an ice bath contained in an insulated bucket, is stirred overnight, during which time the ice melts and the mixture attains room temperature. Fifty ml. of methylene chloride is stirred into the mixture and the solids are filtered and washed with an additional 50 ml. of methylene chloride. The filtrate is separated and the aqueous phase extracted with two 50-ml. portions of methylene chloride. The organic solutions are combined, washed with 25-ml. portions of saturated NaCl, 5% KOH, and saturated NaCl (X2), and then dried (MgSO4). Reduced-pressure evaporation of the solvent from the dried solution gives 13.9 grams (96.5%) of clear, colorless oil which slowly crystallizes, melting point 34.5° to 36.0°C. Attempts to effect recrystallization are not successful. TLC shows the presence of only a trace amount of a contaminant.

Workup

  1. customThe reaction mixture, in an ice bath contained in an insulated bucket
  2. customthe mixture attains room temperature
  3. filtrationthe solids are filtered
  4. washwashed with an additional 50 ml
  5. customThe filtrate is separated
  6. extractionthe aqueous phase extracted with two 50-ml
  7. washwashed with 25-ml
  8. dry with materialportions of saturated NaCl, 5% KOH, and saturated NaCl (X2), and then dried (MgSO4)
  9. customReduced-pressure evaporation of the solvent from the dried solution
  10. customgives 13.9 grams (96.5%) of clear, colorless oil which
  11. customslowly crystallizes
  12. customAttempts to effect recrystallization

Sources & evidence

ORD record
ord-9ce9b6d2d9954d009e208c9d1be117dd
Source dataset
uspto-grants-1976_02
Patent number
US03939263

Reaction notes

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