Acrylamide → HCID 23451639, compound

HRID 1278444Notes

Reaction equation

HRID 1278444 reaction equation
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.[Cl:29][CH2:30][CH2:31][N:32]=[C:33]=[O:34]>C1C=CC=CC=1>[C:1]([NH:5][C:33]([NH:32][CH2:31][CH2:30][Cl:29])=[O:34])(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 6579AcrylamideHCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 314042,6-Di-tert-butyl-4-methylphenol

Product 1

HCID 23451639HCID 23451639, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 71.1 g (1.0 mole) acrylamide, 0.5 g triethylamine, 0.5 g 2,6-ditert-butyl-4-methylphenol and 250 ml benzene is mixed with 110.8 g (1.05 mole) 2-chloroethyl isocyanate and heated in an autoclave over a period of 10 hours to 110° C. The finely crystalline precipitate obtained on cooling is filtered off. 140 g of substance is so obtained. It is recrystallized from 700 ml acetonitrile to yield 115 g (0.65 mole=65% of theory) white crystal needles having a melting point between 156° and 158° C.

Workup

  1. temperatureheated in an autoclave over a period of 10 hours to 110° C
  2. customThe finely crystalline precipitate obtained
  3. temperatureon cooling
  4. filtrationis filtered off
  5. custom140 g of substance is so obtained
  6. customIt is recrystallized from 700 ml acetonitrile
  7. customto yield 115 g (0.65 mole=65% of theory) white crystal needles

Sources & evidence

ORD record
ord-7a2d73adab3b4afea7a866fda8ed4342
Source dataset
uspto-grants-1981_07
Patent number
US04281186

Reaction notes

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