4-Nitrobenzenethiol → HCID 19748757, compound

HRID 2118785Notes

Reaction equation

HRID 2118785 reaction equation
[CH2:1]([CH:4]1[CH:7]([O:8]C(=O)C)[NH:6][C:5]1=O)[CH2:2][CH3:3].[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1)([O-:15])=[O:14]>C1C=CC=CC=1>[CH2:1]([CH:4]1[CH:5]([S:22][C:19]2[CH:20]=[CH:21][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=2)[NH:6][C:7]1=[O:8])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 158094-NitrobenzenethiolHCID 14543786HCID 14543786, compound

Product 1

HCID 19748757HCID 19748757, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Propyl-4-acetoxy azetidinone, 171 mg, is refluxed with 200 mg p-nitrophenyl thiol in 10 ml benzene for 6 hours. The solution is washed 3x with aqueous Na2CO3, dried with MgSO4, filtered and evaporated. The residue is chromatographed on silica gel, eluting with 10:1 CHCl3 -EtOAc, affording 3-propyl-4-p-nitrophenylthioazetidin-2-one.

Workup

  1. washThe solution is washed 3x with aqueous Na2CO3
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is chromatographed on silica gel
  6. washeluting with 10:1 CHCl3 -EtOAc

Sources & evidence

ORD record
ord-cdb187ed9eb145cd8ddb01b124ef7621
Source dataset
uspto-grants-1987_07
Patent number
US04680391

Reaction notes

Loading…