Triethylamine → HCID 23469421, compound

HRID 128347Notes

Reaction equation

HRID 128347 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11].C(N(CC)CC)C.[C:21](Cl)(=[O:25])[C:22]([CH3:24])=[CH2:23]>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][C:21](=[O:25])[C:22]([CH3:24])=[CH2:23])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 6459053N-(4-hydroxy-2-methylphenyl)methanesulfonamide

Product 1

HCID 23469421HCID 23469421, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a mixture of 24.00 g (0.089 mol) of N-(2-methyl-4-hydroxyphenyl)methanesulfonamide, 9.00 g (0.089 mol) of triethylamine, and 150 ml of methylene chloride cooled to approximately 0° C. was added a solution of 9.32 g (0.089 mol) of methacryloyl chloride in 150 ml of methylene chloride and 50 ml of methylene chloride wash over approximately 20 minutes. The reaction mixture was then stirred for another 4 hours at reduced temperature, after which it was washed with 2 percent hydrochloric acid and twice with water. The organic phase was dried over magnesium sulfate, treated with decolorizing carbon, filtered and concentrated to an oil, which crystallized on cooling. The solid was recrystallized from 1:1 dichloroethane:hexane to give 14.7 g (61.3 percent of theory) of N-(2-methyl-4-methacryloyloxyphenyl)methanesulfonamide, m.p.=95° to 97° C.

Workup

  1. washwash over approximately 20 minutes
  2. washafter which it was washed with 2 percent hydrochloric acid and twice with water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. additiontreated with decolorizing carbon
  5. filtrationfiltered
  6. concentrationconcentrated to an oil, which
  7. customcrystallized
  8. temperatureon cooling
  9. customThe solid was recrystallized from 1:1 dichloroethane

Sources & evidence

ORD record
ord-3703aca843de4aa6ba971d1061b0afb5
Source dataset
uspto-grants-1981_03
Patent number
US04259469

Reaction notes

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