Methanesulfonic Acid → p-Acrylamidomethylphenethyl chloride

HRID 65139

Reaction equation

HRID 65139 reaction equation
[CH2:1]([Cl:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([NH:12][C:13](=[O:16])[CH:14]=[CH2:15])O.CS(O)(=O)=O>>[C:13]([NH:12][CH2:10][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][CH2:1][Cl:9])=[CH:4][CH:5]=1)(=[O:16])[CH:14]=[CH2:15]

Participants

4

Conditions

Temperature
15 °C

Procedure

70 parts (0.5 mole) of phenethyl chloride and 51.5 parts (0.51 mole) of N-methylolacrylamide are stirred, in succession, into 300 parts by volume of methanesulfonic acid which has been cooled to 15° C. Stirring is continued for 6 hours at from 15° to 20° C., and hydrolysis is effected by adding 1,500 parts of crushed ice. After the ice has thawed, the product is filtered off and dried in the air to give 84 parts (yield: 75%) of crude p-acrylamidomethylphenethyl chloride, which is recrystallized from methyl alcohol to give a pure product of melting point 145°-147° C.

Workup

  1. customis continued for 6 hours at from 15° to 20° C., and hydrolysis
  2. additionby adding 1,500 parts of crushed ice
  3. filtrationthe product is filtered off
  4. customdried in the air

Sources & evidence

ORD record
ord-a09ae66e3614410880f3d764cf2e144f
Source dataset
uspto-grants-1986_09
Patent number
US04612392

Linked notes

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