Sulfuric Acid → HCID 10704667, compound

HRID 485274Notes

Reaction equation

HRID 485274 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+].C[O:18][C:19]([C:21]1C(N[C:25](=[O:27])[CH:26]=1)=O)=O.S(=O)(=O)(O)O>O>[C:25]1(=[O:27])[N:1]([CH2:2][C:3]2[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=2)[C:19](=[O:18])[CH:21]=[CH:26]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 655264-(Aminomethyl)Benzoic AcidHCID 516892Sodium BicarbonateHCID 22289804HCID 22289804, compound

Product 1

HCID 10704667HCID 10704667, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 3.02 g (20 mmols) portion of 4-aminomethylbenzoic acid was admixed with 100 ml of saturated aqueous solution of NaHCO3, and 3.1 g (20 mmols) of methoxycarbonylmaleimide was added to the mixture at 0° C. After stirring the mixture at 0° for 10 minutes, 200 ml of water was added thereto. The mixture was then stirred at 30° C. for 1 hour and thereafter adjusted to a pH of 2 with concentrated sulfuric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over Na2SO4 and concentrated, affording 3.18 g (yield 87%) of crude 4-maleimidomethylbenzoic acid.

Workup

  1. additionwas added to the mixture at 0° C
  2. stirringThe mixture was then stirred at 30° C. for 1 hour
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fce26b7b35b04087a6e8beaa55faea42
Source dataset
uspto-grants-1985_08
Patent number
US04536391

Reaction notes

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