O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine → HCID 12694259, compound

HRID 426710Notes

Reaction equation

HRID 426710 reaction equation
[N:1]1([C:6]([NH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=2[S:19]([CH3:21])=[O:20])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=C(C)C=C(C)C=1S(O[NH2:34])(=O)=O>C(#N)C>[CH3:21][S:19]([C:10]1[CH:11]=[C:12]([O:17][CH3:18])[C:13]([O:15][CH3:16])=[CH:14][C:9]=1[NH:8][C:6]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:7])(=[NH:34])=[O:20]

Participants

4

Reactant 2

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 12694258HCID 12694258, compound

Product 1

HCID 12694259HCID 12694259, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction mixture containing 51.7 g. of N-pyrrolidinylcarbonyl-2-methylsulfinyl-4,5-dimethoxyaniline and 0.48 mole of O-mesitylenesulfonylhydroxylamine (prepared by the procedure of Tamura et al., J. Org. Chem. 38, 1239, 1973) and 1 l. of acetonitrile was stirred for 48 hours at ambient temperature. The reaction was then concentrated at reduced pressure and the resulting residue dissolved in 2 l. of methylene chloride. The methylene chloride solution was shaken with 1500 ml. of cold water containing 200 ml. of 14 N aqueous ammonium hydroxide. The organic layer was separated, washed with water, and dried. Evaporation of the methylene chloride solvent in vacuo yielded a residue comprising S-methyl-S-[2-(pyrrolidinylcarbonylamino)-4,5-dimethoxyphenyl]sulfoximine. Crystallization of the residue from a chloroform-cyclo hexane solvent mixture yielded 38 g. of crystalline material (70 percent yield) melting at 312°-314° C.

Workup

  1. additionA reaction mixture containing 51.7 g
  2. concentrationThe reaction was then concentrated at reduced pressure
  3. dissolutionthe resulting residue dissolved in 2 l
  4. customThe organic layer was separated
  5. washwashed with water
  6. customdried
  7. customEvaporation of the methylene chloride solvent in vacuo

Sources & evidence

ORD record
ord-b6357f9d4b26445ba68750e38b66c7a2
Source dataset
uspto-grants-1979_10
Patent number
US04171361

Reaction notes

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