Triethylamine → 4-(Phenylsulfamoyl)phenyl 2-methylprop-2-enoate

HRID 1577903Notes

Reaction equation

HRID 1577903 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:7]1([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl>[C:7]1([NH:13][S:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])=[CH:21][CH:22]=2)(=[O:15])=[O:16])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 99212394-hydroxy-N-phenylbenzenesulfonamide

Product 1

HCID 186682844-(Phenylsulfamoyl)phenyl 2-methylprop-2-enoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.31 g (0.03169 mol) of methacryloyl chloride in 60 ml of methylene chloride was added to a solution of 7.9 (0.03169 mol) of N-phenyl-4-hydroxybenzenesulfonamide, 7.06 g (0.0697 mol) of triethylamine and 60 ml of methylene chloride at -5° C. over a period of 15 minutes. The reaction mixture was stirred at reduced temperature for another 2 hours, after which the solution was washed once with 2 percent hydrochloric acid and twice with water. The solution was dried over sodium sulfate, and concentrated in vacuo with warm bath-heating. The resultant oil crystallized on cooling. This solid was recrystallized from ethanol:water (3:2), collected and dried in vacuo. The yield of N-phenyl-4-methacryloyloxybenzenesulfonamide was 7.05 g; m.p.=101° to 102° C.

Workup

  1. washafter which the solution was washed once with 2 percent hydrochloric acid and twice with water
  2. dry with materialThe solution was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. temperaturewith warm
  5. temperaturebath-heating
  6. customThe resultant oil crystallized
  7. temperatureon cooling
  8. customThis solid was recrystallized from ethanol:water (3:2)
  9. customcollected
  10. customdried in vacuo

Sources & evidence

ORD record
ord-c6534ecb24bf4cdb9d3cb53145874e02
Source dataset
uspto-grants-1981_09
Patent number
US04289865

Reaction notes

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