Hydrochloric Acid → HCID 59208438, compound

HRID 2243072Notes

Reaction equation

HRID 2243072 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]([C:9](=[O:11])[CH3:10])=[N:7][CH:6]=[N:5]1.Cl.C([O-])(O)=O.[Na+].[CH3:18][O:19][C:20](=O)[O:21]C>>[CH3:3][N:4]1[C:8]([C:9](=[O:11])[CH2:10][C:20]([O:19][CH3:18])=[O:21])=[N:7][CH:6]=[N:5]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 13568517Ethanone, 1-(1-methyl-1H-1,2,4-triazol-5-yl)- (9CI)

Product 1

HCID 59208438HCID 59208438, compound

Conditions

Temperature
90 °C

Procedure

NaH (7.84 g, 196 mmol of a 60% dispersion in oil) was added portionwise to a solution of 6.18 g (34.5 mmol) of 1-(1-methyl-1H-1,2,4-triazol-5-yl)ethanone (Ohta, S.; Kawasaki, I.; Fukuno, A.; Yamashita, M.; Tada, T.; Kawabata, T. Chem. Pharm. Bull. (1993), 41(7), 1226-31) in 100 ml dimethylcarbonate. The mixture was heated to 90° C. for 2 hour forming a thick slurry. After cooling to room temperature, the mixture was slowly transferred to 1N HCl over ice. The mixture was brought to about pH 7 with NaHCO3, then saturated with NaCl and extracted 4 times with EtOAc. The combined EtOAc layers were dried over anhydrous MgSO4, then concentrated to give an oil that was chromatographed on silica gel (100% DCM followed by gradient elution to 50% EtOAc in DCM). The title compound (5.3 g) was obtained as an oil. NMR: 3.78 (s, 3H), 4.11 (s, 2H), 4.22 (s, 3H), 7.94 (s, 1H).

Workup

  1. customforming a thick slurry
  2. temperatureAfter cooling to room temperature
  3. extractionsaturated with NaCl and extracted 4 times with EtOAc
  4. dry with materialThe combined EtOAc layers were dried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customto give an oil that
  7. customwas chromatographed on silica gel (100% DCM followed by gradient elution to 50% EtOAc in DCM)

Sources & evidence

ORD record
ord-0938d4909789489a8a5fbbd9542285a4
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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