Hydrochloric Acid → 4-[(2-Methylacryloyl)amino]benzoic acid

HRID 1070370Notes

Reaction equation

HRID 1070370 reaction equation
[C:1](O)(=[O:5])[C:2]([CH3:4])=[CH2:3].C(OC(Cl)=O)C.C(N(CC)CC)C.[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1.Cl>C(#N)C>[C:25]([C:24]1[CH:28]=[CH:29][C:21]([NH:20][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])=[CH:22][CH:23]=1)([OH:27])=[O:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 4093Methacrylic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 98590994-[(2-Methylacryloyl)amino]benzoic acidYield 83.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Into a 1 liter flask 600 ml of acetonitrile, 95.2 g (1.1 mol) of methacrylic acid and 120.1 g (1.1 mol) of chloroformic acid ethyl ester were added. To this mixture 111.8 g (1.1 mol) of triethylamine was added over a period of 1 hour in a cold bath. Stirring was continued for 1 hour at room temperature. 137.1 g (1 mol) of 4-aminobezoic acid was added to the mixture. The mixture was heated for 2 hours at 50° C. The mixture was poured into 5 liter of 1% HCl solution. The deposit was filtered, washed and dried to produce 170.9 g of N-(4-carboxyphenyl)-methacrylamide.

Workup

  1. filtrationThe deposit was filtered
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-f3cfdad76aae4b9f8cde6083020a3607
Source dataset
uspto-grants-2005_06
Patent number
US06902860B2

Reaction notes

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