Triethylamine → 4-[(Methylsulfonyl)amino]phenyl prop-2-enoate

HRID 128345Notes

Reaction equation

HRID 128345 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][CH:8]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 4483147N-(4-hydroxyphenyl)methanesulfonamide

Product 1

HCID 234694244-[(Methylsulfonyl)amino]phenyl prop-2-enoateYield 22.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 22.63 g (0.25 mol) of acryloyl chloride in 250 ml of methylene chloride was added over a period of 35 minutes to a mixture of 46.81 g (0.25 mol) of N-(4-hydroxyphenyl)methanesulfonamide, 25.30 g (0.25 mol) of triethylamine and 750 ml of methylene chloride at 0° C. The resultant solution was stirred at reduced temperature for 2.17 hours, washed three times with water and dried over magnesium sulfate. Concentration of the solution in vacuo gave a solid which after two recrystallizations from benzene and drying gave 13.4 g (22.2 percent yield) of N-(4-acryloyloxyphenyl)methanesulfonamide; m.p.=136.5° to 139.5° C.

Workup

  1. washwashed three times with water
  2. dry with materialdried over magnesium sulfate
  3. customConcentration of the solution in vacuo gave a solid which
  4. customafter two recrystallizations from benzene
  5. customdrying

Sources & evidence

ORD record
ord-d75cbae2334b4631b422a24ea60d2e4a
Source dataset
uspto-grants-1981_03
Patent number
US04259469

Reaction notes

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