Triethylamine → 6-(3,4-Dihydro-4-(3,4-dimethoxyphenylcarbonyl)-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydropyridazin-3-one

HRID 1090311Notes

Reaction equation

HRID 1090311 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=3)=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[C:30](Cl)=[O:31]>C(Cl)Cl>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([C:30]([N:4]2[C:5]3[CH:10]=[C:9]([C:11]4[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=4)[CH:8]=[CH:7][C:6]=3[O:1][CH2:2][CH2:3]2)=[O:31])[CH:33]=[CH:34][C:35]=1[O:36][CH3:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77070Veratroyl chlorideHCID 155994076-(3,4-Dihydro-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydropyridazin-3-one

Product 1

HCID 155994096-(3,4-Dihydro-4-(3,4-dimethoxyphenylcarbonyl)-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydropyridazin-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(3,4-Dihydro-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydropyridazin-3-one was dissolved in methylene chloride and 1.1 equivalent of triethylamine. 1.1 equivalent of 3,4-dimethoxybenzoylchloride was added and the mixture heated at reflux for four hours. The solution was washed with sodium bicarbonate solution and then evaporated to dryness. The residue was chromatographed on silica gel eluting with 1:1 ethyl acetate:ethyl ether. The title compound was collected as white needles, mp 207°-208° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for four hours
  3. washThe solution was washed with sodium bicarbonate solution
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel eluting with 1:1 ethyl acetate
  6. customThe title compound was collected as white needles, mp 207°-208° C.

Sources & evidence

ORD record
ord-42048c41a8a146fc8d5feb7ecfc04779
Source dataset
uspto-grants-1992_01
Patent number
US05081242

Reaction notes

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