Ethyl Acetate → Benzyl 5,6-dihydro-1-methyl-2-phenyl-4H-1,3,4-triazine-5-carboxylate

HRID 1651462Notes

Reaction equation

HRID 1651462 reaction equation
I.C[N:3]([C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[NH:6])[NH2:4].Br[C:14](=[CH2:25])[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].N12CCCC1=NCC[CH2:27]2.C(OCC)(=O)C>CN(C)C=O.C1C=CC=CC=1>[CH3:27][N:6]1[CH2:25][CH:14]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[NH:4][N:3]=[C:5]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 13327794N-methylbenzenecarboximidohydrazide hydroiodideHCID 13443472Benzyl 2-bromoprop-2-enoate

Product 1

HCID 23051225Benzyl 5,6-dihydro-1-methyl-2-phenyl-4H-1,3,4-triazine-5-carboxylate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent2×

Procedure

Benzenecarboximidic acid-N-methyl hydrazide monohydroiodide (0.43 g) in dry dimethylformamide (10 ml) and benzyl 2-bromo-prop-2-enoate (0.41 g) in benzene (2.5 ml) were cooled to 0° and stirred together under an atmosphere of nitrogen. A solution of 1,5-diazabicyclo[4.3.0]non-5-ene (0.4 ml) in dimethylformamide (5 ml) was added gradually and the mixture was stirred at 0° for a further 20 minutes. Ethyl acetate (100 ml) was added and the mixture was washed with brine (30 ml) and dried over magnesium sulphate. The solvent was removed at reduced pressure to yield the sub-title product (0.46 g) as an orange oil.

Workup

  1. stirringthe mixture was stirred at 0° for a further 20 minutes
  2. washthe mixture was washed with brine (30 ml)
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-88da4b961b824318bf89175698c207d7
Source dataset
uspto-grants-1990_05
Patent number
US04927822

Reaction notes

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