Acetic Acid → alpha-acetyl-N-isopropyl-3-nitrostyrenesulfonamide

HRID 231599Notes

Reaction equation

HRID 231599 reaction equation
[CH:1]([NH:4][S:5]([CH2:8][C:9](=O)[CH3:10])(=[O:7])=[O:6])([CH3:3])[CH3:2].[N+:12]([C:15]1[CH:16]=C([CH:20]=[CH:21][CH:22]=1)C=O)([O-:14])=[O:13].N1CCCCC1.[C:29](O)(=[O:31])[CH3:30]>C1C=CC=CC=1>[C:29]([C:9]([C:10]1[CH:20]=[CH:21][CH:22]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=1)=[CH:8][S:5]([NH:4][CH:1]([CH3:3])[CH3:2])(=[O:7])=[O:6])(=[O:31])[CH3:30]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 20069376N-isopropyl-2-oxopropanesulfonamide

Product 1

HCID 54206999alpha-acetyl-N-isopropyl-3-nitrostyrenesulfonamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 7.5 g (about 0.04 mol) of N-isopropyl-2-oxopropanesulfonamide and 6.0 g (0.04 mol) of 3-nitrobenzaldehyde in 40 ml of benzene is treated with 0.16 ml of piperidine and 0.48 ml of glacial acetic acid in an analogous manner to that described in Example 1. The oily crude product is triturated with ether, whereby crystallization occurs. There are obtained 2.5 g of α-acetyl-N-isopropyl-3-nitrostyrenesulfonamide in the form of colorless crystals, m.p. 153°-157°.

Workup

  1. customThe oily crude product is triturated with ether, whereby crystallization

Sources & evidence

ORD record
ord-9cdae9abc4f74f0a8be5fa382583ab9a
Source dataset
uspto-grants-1989_07
Patent number
US04847273

Reaction notes

Loading…