Hydrochloric Acid → HCID 86714630, compound

HRID 1409340Notes

Reaction equation

HRID 1409340 reaction equation
[F:1][CH:2]([F:15])[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([O:11]CC)=[O:10])[N:6]=[C:5]1[CH3:14].[OH-].[Na+].Cl>CO.C1COCC1>[F:15][CH:2]([F:1])[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[N:6]=[C:5]1[CH3:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70980533HCID 70980533, compound

Product 1

HCID 86714630HCID 86714630, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-(2,2-difluoroethyl)-2-methyl-1H-imidazole-4-carboxylate (1.375 mmol, 300 mg) was dissolved in methanol (0.5 ml) and THF (4 ml). NaOH 2 M (4.12 mmol, 2.062 ml) was added and the resulting mixture was stirred for 2.5 h at RT. The pH of the mixture was adjusted to about 6 with 5 M HCl and the solvents were evaporated. Ethanol was added and filtered. The filtrate was evaporated. 176 mg of the title compound was obtained. The two isomers formed in the previous reaction were still present. Isomer 1: 1H-NMR (400 MHz, DMSO-d6): δ 2.25 (s, 3H), 4.67-4.80 (m, 2H), 6.09-6.44 (m, 1H), 6.94 (s, 1H). Isomer 2: 1H-NMR (400 MHz, DMSO-d6): δ 2.27 (s, 3H), 4.32-4.44 (m, 2H), 6.17-6.47 (m, 1H), 7.15 (s, 1H).

Workup

  1. customthe solvents were evaporated
  2. additionEthanol was added
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-c72abbee37874359b090e779197e6db4
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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