Triethylamine → 3-methyl-1-(propan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-5-one

HRID 2385631Notes

Reaction equation

HRID 2385631 reaction equation
C([O:3][C:4](=O)/[N:5]=[C:6](\OCC)/[CH3:7])C.Cl.[CH:13]([NH:16][NH2:17])([CH3:15])[CH3:14].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH:13]([N:16]1[C:4](=[O:3])[NH:5][C:6]([CH3:7])=[N:17]1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 855731-Isopropylhydrazine hydrochlorideHCID 13488724ethyl (1Z)-N-ethoxycarbonylethanimidate

Product 1

HCID 1363405273-methyl-1-(propan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-5-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of [1-ethoxy-eth-(Z)-ylidene]-carbamic acid ethyl ester (834 mg, 5.24 mmol) in toluene (15 mL) was added isopropyl hydrazine hydrochloride (637 mg, 5.76 mmol) followed by triethylamine (803 μL, 5.76 mmol). The reaction vessel was sealed and stirred at 45° C. for 45 minutes before the addition of triethylamine (803 μL, 5.76 mmol). The resultant mixture was heated to 90° C. and stirred for 17 hours, then cooled and concentrated in vacuo. The resultant residue was purified by flash chromatography (SiO2, gradient 0% to 8% 2M NH3/MeOH in DCM) to give 2-Isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one as an off white solid (329 mg, 44%). LCMS: RT=2.16 min, [M+Na]+=164

Workup

  1. customThe reaction vessel was sealed
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by flash chromatography (SiO2, gradient 0% to 8% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-f9f65082c93e42798eff6ae2e2e5b47b
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

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