Hydrochloric Acid → 2-(2-Ureidophenyl)acetic acid

HRID 637358Notes

Reaction equation

HRID 637358 reaction equation
C1(C([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][C:13]2=[O:21])=[O:11])=O)CCCCC1.Cl.[OH-:23].[K+]>>[NH:12]([C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:14][C:13]([OH:21])=[O:23])[C:10]([NH2:9])=[O:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13647650N-cyclohexylcarbonyl-2-oxindole-1-carboxamide

Product 1

HCID 136476542-(2-Ureidophenyl)acetic acid

Procedure

A slurry of 2.9 g (0.01 mole) of N-cyclohexylcarbonyl-2-oxindole-1-carboxamide in 50 ml of 1N potassium hydroxide solution was stirred at room temperature for ca. 30 minutes, during which time the solid went into solution. At this point, the reaction mixture was acidified with concentrated hydrochloric acid, with ice cooling, and then it was extracted with ethyl acetate. The extracts were washed with saturated sodium chloride solution, dried (Na2SO4) and evaporated in vacuo to give an oily solid. The oily solid was washed with diisopropyl ether and then it was recrystallized from ethanol to give 70 mg of the title compound, m.p. 174.5° C. (dec.).

Workup

  1. extractionit was extracted with ethyl acetate
  2. washThe extracts were washed with saturated sodium chloride solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give an oily solid
  6. washThe oily solid was washed with diisopropyl ether
  7. customit was recrystallized from ethanol

Sources & evidence

ORD record
ord-b4b20e9e890c4e5fbb8aadcd9a821438
Source dataset
uspto-grants-1985_12
Patent number
US04556672

Reaction notes

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