Hydrochloric Acid → (1-Trityl-1H-imidazol-4-yl)acetic acid

HRID 1844570Notes

Reaction equation

HRID 1844570 reaction equation
[OH-:1].[Na+].[C:3]([N:22]1[CH:26]=[C:25]([CH2:27][C:28]#N)[N:24]=[CH:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH2:30].Cl>CO.C(Cl)Cl>[C:3]([N:22]1[CH:26]=[C:25]([CH2:27][C:28]([OH:30])=[O:1])[N:24]=[CH:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 19099310HCID 19099310, compound

Product 1

HCID 11090087(1-Trityl-1H-imidazol-4-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A 5 N aqueous sodium hydroxide solution (200 mL) was added to a solution of (1-trityl-1H-imidazol-4-yl)acetonitrile (33 g) in methanol (100 mL), and the mixture was heated to reflux for 4 hours. To this reaction solution, water and methylene chloride were added, and the mixture was neutralized with a 1 N aqueous hydrochloric acid solution. Methanol was added thereto until insoluble matter was dissolved, and the organic layer was then separated. The aqueous layer was further subjected to extraction three times with a methylene chloride:methanol (9:1) mixed solvent, and the extracts were combined with the foregoing separated organic layer and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained white solid was washed with a hexane-diisopropyl ether mixed solvent. The solid was dried under reduced pressure to obtain the title compound (34 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. dissolutionuntil insoluble matter was dissolved
  4. customthe organic layer was then separated
  5. extractionThe aqueous layer was further subjected to extraction three times with a methylene chloride:methanol (9:1)
  6. additionmixed solvent
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. washthe obtained white solid was washed with a hexane-diisopropyl ether mixed solvent
  10. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-47b615a035fc426ab4493521967b53fd
Source dataset
uspto-grants-2015_02
Patent number
US08946443B2

Reaction notes

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