Ethanol → 4-Aminobenzoic Acid

HRID 647234Notes

Reaction equation

HRID 647234 reaction equation
[CH2:1]([OH:3])[CH3:2].C=[O:5].[NH2:6][C:7]1[CH:8]=[C:9](C=[CH:14][CH:15]=1)C(O)=O.O>CS(C)=O.CO>[CH:14]1[C:2]([C:1]([OH:5])=[O:3])=[CH:9][CH:8]=[C:7]([NH2:6])[CH:15]=1

Participants

7

Reactant 4

HCID 702Ethanol2×HCID 712FormaldehydeHCID 962WaterHCID 74193-Aminobenzoic Acid

Product 1

HCID 9784-Aminobenzoic Acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 887MethanolSolvent

Procedure

In 70 ml of dimethyl sulfoxide (DMSO) containing 20 percent of ethanol, 1.94 g (0.02 mole) of polymaleimide was dissolved. The resultant solution, with 2 ml of 37 percent formalin solution added thereto, was thermally refluxed at temperatures of 70° to 75° C. To the substance obtained by the thermal reflux was added a solution obtained by dissolving 2.74 g (0.02 mole) of m-aminobenzoic acid in 10 ml of a DMSO solution containing 20 percent of ethanol. This mixed solution was refluxed for two hours. Then, the reaction solution was cooled, and the cooled reaction solution was added to a mixed solution of water and methanol to precipitate insoluble components. The final precipitate was separated by filtration and dissolved in a DMSO solution. The resultant solution was purified by repeated addition of water and methanol in the manner just mentioned, and finally dried. A 2.46-g portion (0.01 mole) of poly-m-maleimidemethyl aminobenzoic acid thus obtained was dissolved in a mixed solution of water and tetrahydrofuran and cooled with water. Separately, 1 g (0.01 mole) of 2-aminothiazole was dissolved in 20 ml of 6 normal hydrochloric acid and cooled. A solution obtained by dissolving 0.74 g of sodium nitrite in a small amount of water was gradually added, while under ice cooling, to the 2-aminothiazole solution to effect diazotization. The resultant diazotized solution was added to the cooled poly-m-maleimidemethyl aminobenzoic acid solution, with the molar ratio of poly-m-maleimidemethyl aminobenzoic acid to the diazotized compound at 1:1, to effect diazo coupling. The precipitate which consequently occurred was separated by filtration and dissolved in dioxane. The resultant solution was poured in a mixed solution of water and methanol. The precipitate was again purified and dried to afford 3.37 g of PTAMMABC (m.p. 280° C.).

Workup

  1. dissolutionwas dissolved
  2. temperaturewas thermally refluxed at temperatures of 70° to 75° C
  3. customTo the substance obtained by the
  4. temperaturethermal reflux
  5. additionwas added a solution
  6. customobtained
  7. temperatureThis mixed solution was refluxed for two hours
  8. temperatureThen, the reaction solution was cooled
  9. customthe cooled reaction solution
  10. customto precipitate insoluble components
  11. customThe final precipitate was separated by filtration
  12. dissolutiondissolved in a DMSO solution
  13. customThe resultant solution was purified
  14. additionaddition of water and methanol in the manner
  15. customfinally dried

Sources & evidence

ORD record
ord-d2b7b0cec323400b986fbbdf4444d82d
Source dataset
uspto-grants-1983_10
Patent number
US04408012

Reaction notes

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