Triethylamine → HCID 23469427, compound

HRID 128349Notes

Reaction equation

HRID 128349 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:24])[CH:22]=[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:24])[CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 17825897N-[(4-Hydroxyphenyl)methyl]methanesulfonamide

Product 1

HCID 23469427HCID 23469427, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 20.1 g (0.10 mol) of N-(4-hydroxybenzyl)methanesulfonamide, 10.1 g (0.10 mol) of triethylamine and 100 ml of methylene chloride cooled to approximately 0° C. was added a solution of 9.0 g (0.10 mol) of acryloyl chloride in 50 ml of methylene chloride over a 10-minute period. Stirring was continued for 30 minutes, and the mixture was filtered. The filtrate was washed twice with water, dried over magnesium sulfate and concentrated in a rotary evaporator. The residue was recrystallized from 100 ml of 1:1 hexane:1,2-dichloroethane. The yield of N-(4-acryloyloxybenzyl)methanesulfonamide was 8.2 g (32.1 percent of theory), m.p.=112° to 115° C.

Workup

  1. filtrationthe mixture was filtered
  2. washThe filtrate was washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in a rotary evaporator
  5. customThe residue was recrystallized from 100 ml of 1:1 hexane

Sources & evidence

ORD record
ord-eefc0a97718144d2871cb6b043666ec1
Source dataset
uspto-grants-1981_03
Patent number
US04259469

Reaction notes

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