Sodium Sulfite → HCID 19605251, compound

HRID 1603666Notes

Reaction equation

HRID 1603666 reaction equation
[C:1]1([S:7][CH:8]2[N:11]([CH2:12][C:13](=[O:22])[CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10](=[O:23])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:32])C=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[C:1]1([S:7]([CH:8]2[N:11]([CH2:12][C:13](=[O:22])[CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10](=[O:23])[CH2:9]2)=[O:32])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium BicarbonateHCID 9905377HCID 9905377, compound

Product 1

HCID 19605251HCID 19605251, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-phenylthio-N-(4-phenyl-2-oxobutyl)azetidin-2-one (2.3 g, 7 mmol) in dichloromethane (80 ml) was cooled to -50 to -60° C. and a solution of m-chloroperbenzoic acid (1.5 g, 9 mmol) in dichloromethane (60 ml) was added dropwise with stirring over 40 min. After a further 2 hr. at -50 to -60° C. another portion of m-chloroperbenzoic acid (61 mg, 0.35 mmol) was added and stirring continued for 30 min. The reaction mixture was then shaken with a mixture of saturated aqueous sodium sulphite and saturated sodium hydrogen carbonate and the organic layer collected, dried (MgSO4) and evaporated. Crystallisation from ether then dichloromethane/ether gave the product as a white crystalline solid, mp 125-6° C., 27% yield 1H NMR δ (CDCl3), 2.78 (2H, m, CH2CO), 2.87 (1H, dd, J=4.7, 15.0 Hz, H3a), 2.94 (2H, m, CH2Ph), 3.42 (1H, dd, J=2.0, 15.0 Hz, H3b), 3.85, 4.46 (each 1H, d, J=18.9 Hz, CH2N), 4.73 (1H, dd, J=2.1, 4.7 Hz, H4), 7.17-7.35 (5H, m, Ph--H), 7.55 (5H, s, SOPh--H). Found: C, 66.7; H, 5.7; N, 4.2%; C19H19NO3S requires: C, 66.8; H, 5.6; N, 4.1%

Workup

  1. waitAfter a further 2 hr
  2. stirringstirring
  3. waitcontinued for 30 min
  4. customthe organic layer collected
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customCrystallisation from ether

Sources & evidence

ORD record
ord-561cb90ebde2453cab6951744d4480db
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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