Dimethylformamide → HCID 86651070, compound

HRID 2190854Notes

Reaction equation

HRID 2190854 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:11]([F:14])([F:13])[F:12])=[CH:9][N:10]=1)[C:5](Cl)=[O:6].CN(C=O)C.[NH2:20][C:21]1[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:24]=[CH:23][C:22]=1[OH:31].C(N(CC)CC)C>O>[C:27]([C:25]1[CH:24]=[CH:23][C:22]([OH:31])=[C:21]([NH:20][C:5](=[O:6])[C:4]2[C:8]([C:11]([F:14])([F:13])[F:12])=[CH:9][N:10]=[C:2]([Cl:1])[CH:3]=2)[CH:26]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 709822-Amino-4-tert-butylphenolHCID 86811334HCID 86811334, compound

Product 1

HCID 86651070HCID 86651070, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.66 g of 2-chloro-5-trifluoromethyl isonicotinic acid and 4 ml of thionyl chloride was heated to reflux for 2.5 hours. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure to give 2-chloro-5-trifluoromethyl isonicotinic acid chloride. A mixture of the resultant 2-chloro-5-trifluoromethyl isonicotinic acid chloride and 4 ml of DMF was added dropwise to a mixture of 0.48 g of 2-amino-4-tert-butylphenol, 0.59 g of triethylamine and 4 ml of DMF while ice-cooling. The reaction mixture was stirred at room temperature for one hour, and stirred while heating at 50° C. for one hour. The mixture was cooled to room temperature, and water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.75 g of N-(5-tert-butyl-2-hydroxyphenyl)-2-chloro-5-trifluoromethylisonicotinamide.

Workup

  1. temperaturecooling
  2. stirringstirred
  3. temperaturewhile heating at 50° C. for one hour
  4. temperatureThe mixture was cooled to room temperature
  5. extractionfollowed by extraction with ethyl acetate twice
  6. washThe combined organic layers were washed with water
  7. dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e56bafa67c4b44c8b4a951ff0af78dd9
Source dataset
uspto-grants-2012_12
Patent number
US08324387B2

Reaction notes

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