Hydrochloric Acid → 2-Chloro-6-(4,6-dimethoxytriazin-2-yloxy)-benzoic acid

HRID 345269Notes

Reaction equation

HRID 345269 reaction equation
CC([O-])(C)C.[K+].[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:9]=1[C:10]([OH:12])=[O:11].Cl[N:19]1[N:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[NH:20]1.Cl>CN(C)C=O.O>[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][N:19]2[N:20]=[C:21]([O:27][CH3:28])[CH:22]=[C:23]([O:25][CH3:26])[NH:24]2)[C:9]=1[C:10]([OH:12])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 925912-Chloro-6-hydroxybenzoic acidHCID 221477162-Chloro-4,6-dimethoxy-triazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 199918532-Chloro-6-(4,6-dimethoxytriazin-2-yloxy)-benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

At 25° C., 20.2 g of potassium tert-butylate is added in portions to 15.5 g of 2-chloro-6-hydroxybenzoic acid in 50 ml of dimethylformamide. Subsequently, 15.7 g of 2-chloro-4,6-dimethoxytriazine is added. The mixture is stirred for 12 hours at 25° C. and poured into cold water, and the resulting mixture is acidified with hydrochloric acid. Extraction is then carried out with ethyl acetate, and the extract is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is stirred with a small amount of diethyl ether, followed by filtration. The residue is dried under reduced pressure (m.p. 128°-131° C.).

Workup

  1. extractionExtraction
  2. dry with materialthe extract is dried over sodium sulfate
  3. customthe solvent is removed under reduced pressure
  4. stirringThe residue is stirred with a small amount of diethyl ether
  5. filtrationfollowed by filtration
  6. customThe residue is dried under reduced pressure (m.p. 128°-131° C.)

Sources & evidence

ORD record
ord-9f0396cf4ca84c5d8c905f274e7561e5
Source dataset
uspto-grants-1991_10
Patent number
US05057143

Reaction notes

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