Hydrochloric Acid → HCID 118161265, compound

HRID 2279279Notes

Reaction equation

HRID 2279279 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[OH:16])/[CH:5]=[C:6]1\[N:7]=[C:8]([CH3:12])[O:9][C:10]\1=O.[CH3:17][NH2:18].C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[OH:16])/[CH:5]=[C:6]1\[N:7]=[C:8]([CH3:12])[N:18]([CH3:17])[C:10]\1=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 11430Potassium CarbonateHCID 118161306HCID 118161306, compound

Product 1

HCID 118161265HCID 118161265, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

(Z)-4-(3-fluoro-4-hydroxybenzylidene)-2-methyloxazole-5(4H)-one (13.2 g, 0.05 mol) was suspended in ethanol (100 mL), and water solution of methylamine (40%, 11.6 g, 0.15 mol) was added. The reaction mixture was stirred at r.t. for 2 hours, then potassium carbonate (13.8 g, 0.1 mol) was added, and the mixture refluxed for 4 hours. Then it was cooled down to r.t., diluted with water (400 mL) and acidified with HCl (10% in water) until the precipitate stopped to form. The precipitate was filtered, washed with cold (−20° C.) ethanol, then diethyl ether and dried under vacuum: 8.78 g. (Yield 75%)

Workup

  1. temperaturethe mixture refluxed for 4 hours
  2. temperatureThen it was cooled down to r.t.
  3. customto form
  4. filtrationThe precipitate was filtered
  5. washwashed with cold (−20° C.) ethanol
  6. dry with materialdiethyl ether and dried under vacuum

Sources & evidence

ORD record
ord-b7ff5d30853348b1b8e567a707d054e8
Source dataset
uspto-grants-2015_09
Patent number
US09133220B2

Reaction notes

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