4-Chlorobenzaldehyde → HCID 54455287, compound

HRID 727752Notes

Reaction equation

HRID 727752 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:20][S:17]([C:14]2[CH:13]=[CH:12][C:11]([Cl:10])=[CH:16][CH:15]=2)(=[O:19])=[O:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 668244-Chlorobenzenesulfonamide

Product 1

HCID 54455287HCID 54455287, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution consisting of 7.03 g (5.0 mmol) of 4-chlorobenzaldehyde, 9.58 g (5.0 mmol) of 4-chlorobenzenesulfonamide, 8 g of 4A molecular sieves and 0.1 g of Amberlite IR-120 in 90 mL of toluene was heated to reflux. The reaction vessel was fitted with a Dean Stark trap which was filled with 4A molecular sieves. The mixture was heated for 4 hours, at which point TLC analysis showed conversion to sulfonimine. The mixture was allowed to cool to room temperature and was filtered. Concentration of the filtrate and subsequent recrystallization of the crude product from CHCl3 -hexane gave 7.84 g (50%) of sulfonimine as a white crystalline material: IR 3090, 1598, 1582, 1553, 1321, 1084 cm1 ; 1H NMR (CDCl3, TMS, 60 MHz) & 9.02 (s, 1), 7.73 (A2B2, 4, Δ√=24 Hz, JAB =8 Hz), 7.67 (A2B2, 4, Δ√=23 Hz, JAB =9 Hz); m.p. 128.0 ° C.

Workup

  1. temperaturewas heated to reflux
  2. customThe reaction vessel was fitted with a Dean Stark trap which
  3. temperatureThe mixture was heated for 4 hours, at which point TLC analysis
  4. filtrationwas filtered
  5. customConcentration of the filtrate and subsequent recrystallization of the crude product from CHCl3 -hexane
  6. customgave 7.84 g (50%) of sulfonimine as a white crystalline material

Sources & evidence

ORD record
ord-6adacd07469242d68a3b337904dba908
Source dataset
uspto-grants-1991_09
Patent number
US05045223

Reaction notes

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