Methanol → Methyl 4-(3-oxo-2,3-dihydro-1,2,4-triazin-6-yl)benzoate

HRID 500216Notes

Reaction equation

C(O[CH:4](OCC)[C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)=O)C.Cl.[NH2:21][NH:22][C:23]([NH2:25])=[O:24].C(N(CC)C(C)C)(C)C.CO>ClCCCl.C(Cl)Cl>[O:24]=[C:23]1[N:25]=[CH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=2)=[N:21][NH:22]1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of methyl 4-(diethoxyacetyl)benzoate (15.4 g, 0.0578 mol), semicarbazide hydrochloride (7.1 g, 0.064 mol), N,N-diisopropylethylamine (12 mL, 0.069 mol) in 1,2-dichloroethane (150 mL), and methanol (2 mL) was heated at 95° C. for 4 h. To the mixture was added an additional 0.1 equivalents of semicarbazide hydrochloride. The mixture was stirred at 95° C. for 1 h. After cooling to RT, the mixture was diluted with methylene chloride and washed with water, brine, dried over Na2SO4, filtered, and concentrated. The residue was refluxed with acetic acid (100 mL) and water (1.0 mL) overnight. The mixture was concentrated to yield quantitative crude material which was directly used in the next step.

Workup

temperatureAfter cooling to RT
washwashed with water, brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
temperatureThe residue was refluxed with acetic acid (100 mL) and water (1.0 mL) overnight
concentrationThe mixture was concentrated
customto yield quantitative crude material which

Sources & evidence

ORD record: ord-5abd7da1945947bf91330e2f575953e7
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

Loading…