Acetic Acid → 2-[4-(3-Bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid

HRID 585126Notes

Reaction equation

HRID 585126 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([N:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])C(C#N)=[N:14]2)=[CH:8][C:7]=1[CH3:23].Cl.[C:30]([OH:33])(=[O:32])[CH3:31]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[O:5][C:6]1[C:7]([CH3:23])=[CH:8][C:9]([N:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])[C:31]([C:30]([OH:33])=[O:32])=[N:14]2)=[CH:10][C:11]=1[CH3:12]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 223395632-[4-(3-Bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile

Product 1

HCID 223394382-[4-(3-Bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid

Procedure

A solution of 2-[4-(3-bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile (700 mg) of EXAMPLE 1, hydrochloric acid (5 ml) and acetic acid (5 ml) was heated to 120° C. for 3 h. The resulting solids were filtered, rinsed and dried to afford the title compound as a brown solid (593 mg). MS Calc.: 461.0; Found: 459.7 (M−1).

Workup

  1. filtrationThe resulting solids were filtered
  2. washrinsed
  3. customdried

Sources & evidence

ORD record
ord-22467f080c3d44e98ebabec28b4f61f8
Source dataset
uspto-grants-2005_08
Patent number
US06930107B2

Reaction notes

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