Hydrochloric Acid → 1-Trityl-1H-imidazole-4-carboxylic acid

HRID 2355287Notes

Reaction equation

HRID 2355287 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[N:8]=[CH:9][N:10]([C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=1)=[O:6].Cl>O1CCCC1.CO>[C:12]([N:10]1[CH:11]=[C:7]([C:5]([OH:6])=[O:4])[N:8]=[CH:9]1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10429115methyl 1-trityl-1H-imidazole-4-carboxylate

Product 1

HCID 105701171-Trityl-1H-imidazole-4-carboxylic acidYield 74.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 1N sodium hydroxide (22.8 mL, 22.8 mmol) to 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (2.8 g, 7.60 mmol) in tetrahydrofuran (20 mL) and methanol (20 mL) at room temperature. Stir the reaction mixture at room temperature for 5 hrs. Acidify the reaction mixture with 5N aqueous hydrochloride to pH about 6. Filter and dry the solid to give the title compound as a white solid (2 g, 5.64 mmol).

Workup

  1. filtrationFilter
  2. customdry the solid

Sources & evidence

ORD record
ord-a29b83a0b00045a29b99e62be82cf6b7
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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