Triethylamine → 4-((Methylamino)sulfonyl)phenyl 2-methyl-2-propenoate
Reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].C(N(CC)CC)C.[C:20](Cl)(=[O:24])[C:21]([CH3:23])=[CH2:22]>C(Cl)Cl>[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:20](=[O:24])[C:21]([CH3:23])=[CH2:22])=[CH:8][CH:7]=1)(=[O:4])=[O:5]Participants
Procedure
To a solution of 15.00 g (0.08 mole) of N-methyl-4-hydroxybenzenesulfonamide, 8.11 g (0.08 mole) of triethylamine and 200 ml of methylene chloride cooled to 0° C. was added a solution of 8.37 g (0.08 mole) of methacryloyl chloride in 100 ml of methylene chloride over a period of approximately 30 minutes. The solution was then stirred for another 3 hours with cooling; washed once with 100 ml of 2 percent HCl solution, and twice with water; dried over magnesium sulfate and concentrated in vacuo in a warm water bath. The resultant solid was recrystallized from 150 ml of ethyl alcohol:water (1:1) with filtering through diatomaceous earth. Collection of the white solid and drying at room temperature in vacuo gave 16.20 g (79.9 percent of theory) of N-methyl-4-methacryloyloxybenzenesulfonamide; m.p.=106° to 107° C.
Workup
- temperaturewith cooling
- washwashed once with 100 ml of 2 percent HCl solution
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo in a warm water bath
- customThe resultant solid was recrystallized from 150 ml of ethyl alcohol:water (1:1)
- filtrationwith filtering through diatomaceous earth
- customCollection of the white solid
- customdrying at room temperature in vacuo
Sources & evidence
- ORD record
- ord-18cb54244dab4e20a339265cd200cee2
- Source dataset
- uspto-grants-1982_06
- Patent number
- US04335254
Reaction notes
Loading…