Triethylamine → HCID 23469426, compound

HRID 128348Notes

Reaction equation

HRID 128348 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:21](Cl)(=[O:25])[C:22]([CH3:24])=[CH2:23]>C(Cl)Cl>[C:21]([O:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1)(=[O:25])[C:22]([CH3:24])=[CH2:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 17825897N-[(4-Hydroxyphenyl)methyl]methanesulfonamide

Product 1

HCID 23469426HCID 23469426, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 6.04 g (0.03 mol) of N-(4-hydroxybenzyl)methanesulfonamide, 3.04 g (0.03 mol) of triethylamine, and 30 ml of methylene chloride was cooled to approximately 0° C. To this mixture was added a solution of 3.14 g (0.03 mol) of methacryloyl chloride in 15 ml of methylene chloride over approximately 5 minutes. The mixture was stirred for an additional 15 minutes and filtered. The filtrate was washed twice with water, dried over magnesium sulfate and concentrated in a rotary evaporator. The solid residue was recrystallized from 1:1 hexane:1,2-dichloroethane. The yield of N-(4-methacryloyloxybenzyl)methanesulfonamide was 3.0 g (37.13 percent of theory), m.p.=101° to 102.5° C.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in a rotary evaporator
  5. customThe solid residue was recrystallized from 1:1 hexane

Sources & evidence

ORD record
ord-4ffd12e686464993a8b006dd3d649006
Source dataset
uspto-grants-1981_03
Patent number
US04259469

Reaction notes

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