Methacryloyl chloride → HCID 18668254, compound

HRID 128343Notes

Reaction equation

HRID 128343 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[C:13](Cl)(=[O:17])[C:14]([CH3:16])=[CH2:15]>C(Cl)Cl>[C:13]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10])(=[O:17])[C:14]([CH3:16])=[CH2:15]

Participants

4

Reactant 2

HCID 13528Methacryloyl chlorideHCID 316696N-(2-hydroxyphenyl)methanesulfonamide

Product 1

HCID 18668254HCID 18668254, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 10.12 g (0.10 mol) of triethylamie, 18.72 g (0.10 mol) of N-(2-hydroxyphenyl)methanesulfonamide and 300 ml of methylene chloride cooled to 0° C. was added a solution of 10.45 g (0.10 mol) of methacryloyl chloride in 100 ml of methylene chloride over a 15-minute period. After stirring 2 hours at reduced temperature, the solution was washed three times with water, dried over magnesium sulfate and concentrated to an oil. On cooling and scratching, the oil crystallized. Recrystallization from 1:1 benzene:hexane gave a white solid which was collected, washed with 1:1 benzene:hexane, and dried at room temperature in vacuo. The yield of N-(2-methacryloyloxyphenyl)methanesulfonamide was 10.4 g (40.7 percent); m.p.=88° to 90° C.

Workup

  1. washthe solution was washed three times with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to an oil
  4. temperatureOn cooling
  5. customthe oil crystallized
  6. customRecrystallization from 1:1 benzene
  7. customhexane gave a white solid which
  8. customwas collected
  9. washwashed with 1:1 benzene
  10. dry with materialhexane, and dried at room temperature in vacuo

Sources & evidence

ORD record
ord-b41cdd2963004bd183a6fbb271b1f286
Source dataset
uspto-grants-1981_03
Patent number
US04259469

Reaction notes

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