4-Aminosalicylic Acid → HCID 68178775, compound

HRID 571579Notes

Reaction equation

HRID 571579 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.[C:12]([O:17][CH2:18][CH2:19][N:20]=[C:21]=[O:22])(=[O:16])[C:13]([CH3:15])=[CH2:14]>CC(C)=O>[OH:11][C:4]1[CH:3]=[C:2]([NH:1][C:21]([NH:20][CH2:19][CH2:18][O:17][C:12](=[O:16])[C:13]([CH3:15])=[CH2:14])=[O:22])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 46494-Aminosalicylic Acid2×HCID 354092-Isocyanatoethyl methacrylate

Product 1

HCID 68178775HCID 68178775, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

15.3 g (0.1 mol) 4-amino-2-hydroxy-benzoic acid was dissolved in 100 ml acetone. 17.06 g (0.11 mol) 2-isocyanatoethyl methacrylate was dissolved in 15 ml acetone and added dropwise to the 4-amino-2-hydroxy-benzoic acid solution. The temperature rose to 32° C. during the addition. The reaction was allowed to continue for two hours at room temperature. The solvent was evaporated under reduced pressure. The residue was dissolved in a mixture 200 ml acetone and 50 ml methanol. The solution was added to 1 l water while stirring. 2-hydroxy-4-{3-[2-(2-methyl-acryloyloxy)-ethyl]-ureido}-benzoic acid precipitated from the medium and was isolated by filtration. 2-hydroxy-4-{3-[2-(2-methyl-acryloyloxy)-ethyl]-ureido}-benzoic acid was washed twice with 150 ml water and dried. 28.5 g (92.5%) of 2-hydroxy-4-{3-[2-(2-methyl-acryloyloxy)-ethyl]-ureido}-benzoic acid was isolated (melting point: 208-210° C.)

Workup

  1. additionThe temperature rose to 32° C. during the addition
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in a mixture 200 ml acetone and 50 ml methanol
  4. additionThe solution was added to 1 l water
  5. custom2-hydroxy-4-{3-[2-(2-methyl-acryloyloxy)-ethyl]-ureido}-benzoic acid precipitated from the medium
  6. customwas isolated by filtration
  7. wash2-hydroxy-4-{3-[2-(2-methyl-acryloyloxy)-ethyl]-ureido}-benzoic acid was washed twice with 150 ml water
  8. customdried

Sources & evidence

ORD record
ord-b4abdff0d18a4963890f6a14ad5a32c0
Source dataset
uspto-grants-2015_05
Patent number
US09029066B2

Reaction notes

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