Ethyl Acetate → HCID 22339462, compound

HRID 585145Notes

Reaction equation

HRID 585145 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:20]2[C:25](=[O:26])[NH:24][C:23](=[O:27])[CH:22]=[N:21]2)[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([CH:17]=[O:18])[CH:10]=1.B(Cl)(Cl)Cl.C(OCC)(=O)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:20]2[C:25](=[O:26])[NH:24][C:23](=[O:27])[CH:22]=[N:21]2)[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:17]=[O:18])[CH:10]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25135Boron TrichlorideHCID 22339565HCID 22339565, compound

Product 1

HCID 22339462HCID 22339462, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 2-[3,5-dichloro-4-(3-formyl-4-methoxy-phenoxy)-phenyl]-2H-[1,2,4]triazine-3,5-dione (0.4 g) in dichloromethane (10 mL) was added 1M boron trichloride in dichloromethane (4 mL). The resulting orange slurry was stirred at ambient temperature for 5 h, ice added and the reaction stirred an additional 1 h. The two phase solution was diluted into ethyl acetate and washed with water, brine, dried (Na2SO4), concentrated in vacuo to afford the title compound of Step B as an off-white solid, 0.4 g (m.p. 146-150° C.).

Workup

  1. additionice added
  2. stirringthe reaction stirred an additional 1 h
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8db8284acf164afaad40dd55e831db88
Source dataset
uspto-grants-2005_08
Patent number
US06930107B2

Reaction notes

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