Hydrochloric Acid → HCID 86714632, compound

HRID 1409343Notes

Reaction equation

HRID 1409343 reaction equation
[OH:1][C@H:2]([CH3:15])[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>[OH:1][C@H:2]([CH3:15])[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 86714631HCID 86714631, compound

Product 1

HCID 86714632HCID 86714632, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(R)-Ethyl 1-(2-hydroxypropyl)-2-methyl-1H-imidazole-4-carboxylate (2.474 mmol, 525 mg) was dissolved in methanol (1 ml) and THF (8 ml). NaOH 2 M (7.42 mmol, 3.71 ml) was added and the resulting mixture was stirred overnight at RT. The pH of the mixture was adjusted to about 5 with 1M HCl and the solvents were evaporated. Ethanol was added and the salts were removed by filtration. The filtrate was evaporated. 393 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.03 (m, 6H), 2.30 (s, 3H), 3.71-3.80 (m, 1H), 3.81-3.97 (m, 2H), 4.95 (bs), 7.67 (s, 1H).

Workup

  1. customthe solvents were evaporated
  2. additionEthanol was added
  3. customthe salts were removed by filtration
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-9520b08b33c94e1dbcbcedce322f3ff8
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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