Sodium Hydroxide → HCID 59674008, compound

HRID 1391456Notes

Reaction equation

HRID 1391456 reaction equation
[CH3:1][S:2]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)(=[N:4][N+:5]([O-:7])=[O:6])=[O:3].[OH-].[Na+]>C1COCC1.Cl>[NH2:14][C:10]1[CH:9]=[C:8]([S:2]([CH3:1])(=[N:4][N+:5]([O-:7])=[O:6])=[O:3])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59674000HCID 59674000, compound

Product 1

HCID 59674008HCID 59674008, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 100 mg (0.41 mmol) of (RS)-S-methyl-N-nitro-S-(3-nitrophenyl)sulfoximide in 8 ml of THF is mixed at room temperature with 3.1 ml of an approximately 10% solution of Ti(III)Cl in 20-30% hydrochloric acid. After 1 hour, another 1.0 ml of the approximately 10% solution of Ti(III)Cl in 20-30% hydrochloric acid is added, and it is stirred for another 45 minutes at room temperature. The batch is made basic with 1N NaOH solution and extracted with ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The residue that is obtained is purified by chromatography (DCM/EtOH 95:5). 40 mg (0.19 mmol, corresponding to 45% of theory) of the product is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe residue that is obtained
  6. customis purified by chromatography (DCM/EtOH 95:5)
  7. custom40 mg (0.19 mmol, corresponding to 45% of theory) of the product is obtained

Sources & evidence

ORD record
ord-84d4920613cd4a73aab207073cc5bd92
Source dataset
uspto-grants-2008_03
Patent number
US07338958B2

Reaction notes

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