N-(1-Cyano-1-methylethyl)-2-(methylthio)ethanesulfonamide → HCID 13799780, compound

HRID 1906390Notes

Reaction equation

HRID 1906390 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[C:7]([C:9]([NH:12][S:13]([CH2:16][CH2:17][S:18][CH3:19])(=[O:15])=[O:14])([CH3:11])[CH3:10])#[N:8]>O.CO>[C:7]([C:9]([NH:12][S:13]([CH2:16][CH2:17][S:18]([CH3:19])=[O:2])(=[O:14])=[O:15])([CH3:11])[CH3:10])#[N:8]

Participants

5

Reactant 2

HCID 13799779N-(1-Cyano-1-methylethyl)-2-(methylthio)ethanesulfonamideHCID 23667635Sodium periodate

Product 1

HCID 13799780HCID 13799780, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

To a stirred solution of 4.27 g (0.020 moles) sodium metaperiodate in 40 ml water which had been cooled to about 0° C. in an ice bath, 4.10 g (0.0184 mole) N-(2-cyano-2-propyl)-2-methylthioethylsulfonamide (the product of Example 27) in about 10 ml methanol was added slowly. Initially, the mixture was homogeneous, but after the addition was complete (after about three minutes), a thick precipitate formed. Additional methanol (15 ml) and water (60 ml) was added, thinning the precipitate to allow stirring. The mixture was stirred overnight in a slowly melting ice bath and then filtered. The solid was washed with methylene chloride. The filtrate was washed three times with 50 ml methylene chloride. The methylene chloride fractions were combined and evaporated to dryness to give 2.2 g of crude product, as a white solid. Recrystallization from ethanol gave 1.6 g of the above-identified product as a solid, melting point 142°-144° C.

Workup

  1. additionafter the addition
  2. custom(after about three minutes)
  3. customa thick precipitate formed
  4. stirringThe mixture was stirred overnight in a slowly melting ice bath
  5. filtrationfiltered
  6. washThe solid was washed with methylene chloride
  7. washThe filtrate was washed three times with 50 ml methylene chloride
  8. customevaporated to dryness
  9. customto give 2.2 g of crude product
  10. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-c67f8acf8a2d45729c92d4dd7ef0eab5
Source dataset
uspto-grants-1987_03
Patent number
US04652556

Reaction notes

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