Hydrochloric Acid → HCID 86714636, compound

HRID 1409351Notes

Reaction equation

HRID 1409351 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 86714635HCID 86714635, compound

Product 1

HCID 86714636HCID 86714636, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-Ethyl 1-(2-hydroxypropyl)-2-methyl-1H-imidazole-4-carboxylate (0.655 mmol, 139 mg) was dissolved in methanol (0.5 ml) and THF (4 ml). NaOH 2 M (1.965 mmol, 0.982 ml) was added and the resulting mixture was stirred overnight at RT. The mixture was acidified (pH-5) with 1 M HCl and evaporated. Ethanol was added and the salts were removed by filtration. The filtrate was evaporated. 112 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.06 (d, 3H), 2.30 (s, 3H), 3.70-3.91 (m, 4H), 7.59 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-6d8b5f080c4c4945a0f2f4fc9c5aab4b
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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