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

HRID 2063271Notes

Reaction equation

HRID 2063271 reaction equation
C[O:2][C:3]([C:5]1[NH:6][CH:7]=[N:8][CH:9]=1)=[O:4].C(N(CC)CC)C.Cl[C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Li+].Cl>C(Cl)Cl.O>[C:18]([N:8]1[CH:9]=[C:5]([C:3]([OH:2])=[O:4])[N:6]=[CH:7]1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 565661Methyl 4-imidazolecarboxylate

Product 1

HCID 105701171-Trityl-1H-imidazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3H-Imidazole-4-carboxylic acid methyl ester (9.86 g, 78.2 mmol) is taken up in 150 mL DCM, triethylamine (11.9 mL, 86.0 mmol) is added and the reaction mixture is stirred for 5 min at RT. Chlorotriphenylmethane (24.0 g, 86.0 mmol) is added and the reaction mixture is stirred overnight at RT. The reaction mixture is extracted with an aqueous 5% NaHCO3 solution, the organic phase is dried over MgSO4 and concentrated under reduced pressure. The residue (20.7 g) is taken up in 100 mL MeOH, a solution of lithium hydroxide (4.80 g, 24.0 mmol) in 20 mL water is added drop wise and the reaction mixture is stirred over weekend at RT. The reaction mixture is acidified to pH 4 with 6N hydrochloric acid, 200 mL DCM is added and the two phase mixture is stirred vigorously. The phases are separated and the organic phase is dried over MgSO4 and concentrated under reduced pressure. Yield: 19.2 g. HPLC-MS: double peak tR=2.55/2.67 min, (M−H)−=353.

Workup

  1. stirringthe reaction mixture is stirred overnight at RT
  2. extractionThe reaction mixture is extracted with an aqueous 5% NaHCO3 solution
  3. dry with materialthe organic phase is dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. stirringthe reaction mixture is stirred over weekend at RT
  6. additionis added
  7. stirringthe two phase mixture is stirred vigorously
  8. customThe phases are separated
  9. dry with materialthe organic phase is dried over MgSO4
  10. concentrationconcentrated under reduced pressure
  11. custom2.67 min, (M−H)−=353

Sources & evidence

ORD record
ord-ae7d40e5f3a74283aa13cd17a97c1e6b
Source dataset
uspto-grants-2012_10
Patent number
US08288379B2

Reaction notes

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