Hydrochloric Acid → HCID 178524794, compound

HRID 624650Notes

Reaction equation

HRID 624650 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[C:11]([C:13]([O:15]CC)=[O:14])[N:12]=2)=[C:4]([F:18])[CH:3]=1.[OH-].[Na+].Cl>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[C:11]([C:13]([OH:15])=[O:14])[N:12]=2)=[C:4]([F:18])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178469887HCID 178469887, compound

Product 1

HCID 178524794HCID 178524794, compoundYield 10.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl 2-(4-chloro-2-fluorophenyl)-1H-imidazole-4-carboxylate 41 (175 g, 4.3 mol) in THF (1 L, 6 vol) and H2O (500 mL, 3 vol) was added NaOH (78 g, 1.95 mol, 3.0 eq), and the reaction was stirred at 65° C. for 48 h till it completed (checked by LC-MS). Adjust the mixture with 2 N HCl to pH=5, and product was separated out as a yellow solid, filtered to give 210 g wet cake, the wet cake was washed with H2O (300 mL), DCM (3×300 mL), PE (500 mL), and dried to afford 110 g pure 2-(4-chloro-2-fluorophenyl)-1H-imidazole-4-carboxylic acid 42 (CAS Reg. No. 1260649-87-3) (Scheme 15). 1H NMR (DMSO d6) δ: 12.8 (br s), 8.0, 7.9 (br s), 7.46, 7.4 (m),

Workup

  1. customwas separated out as a yellow solid
  2. filtrationfiltered
  3. customto give 210 g wet cake
  4. washthe wet cake was washed with H2O (300 mL), DCM (3×300 mL), PE (500 mL)
  5. customdried

Sources & evidence

ORD record
ord-15fd91c359f440d29b386eeffe92f78d
Source dataset
uspto-grants-2016_04
Patent number
US09303043B2

Reaction notes

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