Hexane → HCID 23469420, compound

HRID 128346Notes

Reaction equation

HRID 128346 reaction equation
[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[S:3]([CH3:6])(=[O:5])=[O:4].C(N(CC)CC)C.[C:21](Cl)(=[O:25])[C:22]([CH3:24])=[CH2:23].CCCCCC>C(Cl)Cl>[C:21]([O:13][C:10]1[CH:11]=[CH:12][C:7]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:4])=[O:5])=[CH:8][CH:9]=1)(=[O:25])[C:22]([CH3:24])=[CH2:23]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 198964Methanesulfonamide, N-(4-hydroxyphenyl)-N-methyl- (9CI)

Product 1

HCID 23469420HCID 23469420, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 20.13 g (0.10 mol) of N-methyl-N-(4-hydroxyphenyl)methanesulfonamide, 10.12 g (0.10 mol) of triethylamine 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 50 ml of methylene chloride for a 15-minute period. The solution was stirred for another 2 hours at reduced temperature, washed three times with water, dried over magnesium sulfate and concentrated to a white solid. Recrystallization from 500 ml of 1:1 benzene:hexane gave 16.4 g (60.9 percent yield) of N-(4-methacryloyloxyphenyl)-N-methylmethanesulfonamide, m.p.=126° to 127° C.

Workup

  1. washwashed three times with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to a white solid
  4. customRecrystallization from 500 ml of 1:1 benzene

Sources & evidence

ORD record
ord-3283338bca594e9e9b295a91d5d8e873
Source dataset
uspto-grants-1981_03
Patent number
US04259469

Reaction notes

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