Salicylic Acid → HCID 67586072, compound

HRID 1938130Notes

Reaction equation

HRID 1938130 reaction equation
[C:1]([C:4]1([OH:19])[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:18])[C:15]([CH3:17])=[CH2:16])=[CH:9][CH:5]1[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O.[C:43](O)(=O)[C:44]1[C:45](=[CH:47][CH:48]=[CH:49][CH:50]=1)[OH:46].NC(N)=O.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:1]([C:4]1([OH:19])[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:18])[C:15]([CH3:17])=[CH2:16])=[CH:9][CH:5]1[C:6]([O:8][CH2:43][C:44]1[C:45](=[CH:47][CH:48]=[CH:49][CH:50]=1)[OH:46])=[O:7])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 338Salicylic AcidHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 67586054HCID 67586054, compoundHCID 86734857HCID 86734857, compound

Product 1

HCID 67586072HCID 67586072, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-acetyl-5-methacrylamidosalicylic acid (1 part by mole), dicyclohexyl carbodiimide (1.1 part by mole) in dry dichloromethane is added N-hydroxysuccinimide. To the solution is further added salicylic acid (1.1 part by mole). The solution is stirred at room temperature overnight. After the reaction, the precipitate including dicyclohexyl carbodiimide urea is removed by filtration. The solution is washed by distilled water three times, by an aqueous solution of 5% by weight of acetic acid three times, and further by distilled water three times. The solution is filtrated again to remove the precipitate. The solvent is removed by evaporation, and the residue is recrystallized to give salicyl 2-acetyl-5-methacrylamidosalicylate.

Workup

  1. customAfter the reaction
  2. customis removed by filtration
  3. washThe solution is washed
  4. distillationby distilled water three times
  5. distillationby an aqueous solution of 5% by weight of acetic acid three times, and further by distilled water three times
  6. filtrationThe solution is filtrated again
  7. customto remove the precipitate
  8. customThe solvent is removed by evaporation
  9. customthe residue is recrystallized

Sources & evidence

ORD record
ord-d13e9724d51f4af686df1d16c7518e8d
Source dataset
uspto-grants-1997_12
Patent number
US05693320

Reaction notes

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