Hydrochloric Acid → HCID 58572498, compound

HRID 1927299Notes

Reaction equation

HRID 1927299 reaction equation
[Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN1CCOCC1.Cl.[CH3:21][O:22][NH:23][CH3:24].[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.Cl>C(#N)C>[Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:23]([O:22][CH3:21])[CH3:24])=[O:6]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 1451622-Bromo-3-methoxybenzoic acidHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

Product 1

HCID 58572498HCID 58572498, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromo-3 methoxy benzoic acid (14.2 g, 61.5 mmol) was dissolved in acetonitrile (250 mL), added with 4-methylmorpholine (13.5 mL, 123 mmol), N-methoxy methanamine hydrochloride (7.19 g, 73.8 mmol), and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride (20.4 g, 73.8 mmol), and stirred for 17 hours at room temperature. 1 N aqueous hydrochloric acid solution was added to the reaction solution, which was then extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 85:15 to 25:75, V/V) to give the title compound as a colorless oily substance (16.8 g, quantitative).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 85:15 to 25:75, V/V)

Sources & evidence

ORD record
ord-cc2085f9575a43f2bd04b14129c0ba36
Source dataset
uspto-grants-2012_05
Patent number
US08183272B2

Reaction notes

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