Chloroacetic Acid → HCID 20556480, compound

HRID 1660414Notes

Reaction equation

HRID 1660414 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])=[CH:4][CH:3]=1.Cl[CH2:22][C:23]([OH:25])=[O:24].C(O)C.[OH-].[K+].Cl>C(O)C>[C:23]([CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])=[CH:6][CH:7]=1)([OH:25])=[O:24]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 177325-(4-Hydroxyphenyl)-5-phenylhydantoinHCID 21946426Potassium hydroxide ethanol

Product 1

HCID 20556480HCID 20556480, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

400 mg of 5-(p-hydroxyphenyl)-5-phenylhydantoin in 4 ml of absolute ethanol was mixed with 140 mg of chloroacetic acid in 3.5 ml of 1 N-potassium hydroxide ethanol solution and then the mixture was refluxed for 22 hours. After cooled, the mixture was acidified with 0.33 ml of 5 N-hydrochloric acid, followed by distillation to remove the ethanol. Then 20 ml of distilled water was added and the pH value was adjusted to 1.0-2.0 with 5 N-hydrochloric acid. The solution obtained was extracted four times with 5 ml of ethyl acetate and dried with anhydrous sodium sulfate. Then it was dissolved in 2 ml of chloroform-methanol (2:1, v/v) solution and the solution was fractionated through a 2.0×40 cm silica gel column. The second fraction was collected. 5-(p-carboxymethoxyphenyl)-5-phenylhydantoin (CMPPH) was obtained by evaporating the second fraction and dried on calcium chloride under vacuo.

Workup

  1. temperaturethe mixture was refluxed for 22 hours
  2. temperatureAfter cooled
  3. distillationfollowed by distillation
  4. customto remove the ethanol
  5. additionThen 20 ml of distilled water was added
  6. customThe solution obtained
  7. extractionwas extracted four times with 5 ml of ethyl acetate
  8. dry with materialdried with anhydrous sodium sulfate
  9. dissolutionThen it was dissolved in 2 ml of chloroform-methanol (2:1
  10. customThe second fraction was collected

Sources & evidence

ORD record
ord-1c62441bdca24616a0ea22dbd7ce7f2d
Source dataset
uspto-grants-1981_12
Patent number
US04308026

Reaction notes

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