Boron Trichloride → HCID 22339735, compound

HRID 585136Notes

Reaction equation

HRID 585136 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:27]2[C:32](=[O:33])[NH:31][C:30](=[O:34])[CH:29]=[N:28]2)[CH:5]=[C:6]([CH3:26])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:10]=1.B(Cl)(Cl)Cl>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:27]2[C:32](=[O:33])[NH:31][C:30](=[O:34])[CH:29]=[N:28]2)[CH:5]=[C:6]([CH3:26])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([S:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH:10]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 22339388HCID 22339388, compound

Product 1

HCID 22339735HCID 22339735, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-{3-chloro-4-[3-(benzenesulfonyl)-4-methoxy-phenoxy]-5-methyl-phenyl}-2H-[1,2,4]triazine-3,5-dione (0.66 g) in dichloromethane (12 mL) was added boron trichloride (8 mL, 1M in dichloromethane) and the resulting solution was stirred for 4 h. The reaction solution was poured onto ice, allowed to stir for 1 h, the phases separated and the aqueous layer washed with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated to afford the title compound of this EXAMPLE as a tan foam, 0.52 g. m.p. 78-81° C.

Workup

  1. additionThe reaction solution was poured onto ice
  2. stirringto stir for 1 h
  3. customthe phases separated
  4. washthe aqueous layer washed with dichloromethane
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2a6d021a9c3f4c4dafc4e12677bbd6f2
Source dataset
uspto-grants-2005_08
Patent number
US06930107B2

Reaction notes

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