Hydrochloric Acid → HCID 86666614, compound

HRID 587831Notes

Reaction equation

HRID 587831 reaction equation
CN(C)C=O.N(OC(C)(C)C)=O.Cl.N[C:15]1[CH:16]=[C:17]([CH:40]=[CH:41][C:42]=1[N:43]1[CH:47]=[N:46][CH:45]=[N:44]1)[C:18]([NH:20][C:21]1[C:26]([CH3:27])=[CH:25][C:24]([C:28]([F:37])([C:33]([F:36])([F:35])[F:34])[C:29]([F:32])([F:31])[F:30])=[CH:23][C:22]=1[CH2:38][CH3:39])=[O:19]>O>[CH2:38]([C:22]1[CH:23]=[C:24]([C:28]([F:37])([C:33]([F:34])([F:35])[F:36])[C:29]([F:31])([F:32])[F:30])[CH:25]=[C:26]([CH3:27])[C:21]=1[NH:20][C:18](=[O:19])[C:17]1[CH:40]=[CH:41][C:42]([N:43]2[CH:47]=[N:46][CH:45]=[N:44]2)=[CH:15][CH:16]=1)[CH3:39]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 10906Tert-Butyl nitriteHCID 50940482HCID 50940482, compound

Product 1

HCID 86666614HCID 86666614, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

N,N-dimethylformamide (3 ml) was heated to 65° C. and added with tert-butyl nitrite (0.15 g). To the solution, an N,N-dimethylformamide solution (2 ml) in which 3-amino-N-[2-ethyl-4-(1,1,1,2,3, 3,3-heptafluoropropan-2-yl)-6-methylphenyl]-4-(1H-1,2,4-triazol-1-yl) benzamide (0.5 g) has been dissolved was slowly added dropwise, while maintaining the temperature of 65° C. After confirming that no more gas is generated, the mixture was adjusted to room temperature and added with a mixture including 2N hydrochloric acid and a small amount of ice. The mixture was diluted with water and extracted twice with ethyl acetate. The organic phases were combined, washed with 2N hydrochloric acid, and dried over magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-4-(1H-1,2,4-triazol-1-yl)benzamide (0.31 g, yield 61%).

Workup

  1. additionwas slowly added dropwise
  2. customwas adjusted to room temperature
  3. additionadded with a mixture
  4. extractionextracted twice with ethyl acetate
  5. washwashed with 2N hydrochloric acid
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtering off the drying agent
  8. distillationthe solvent was distilled off under reduced pressure
  9. customto obtain a crude product
  10. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-8d9eef45e2af4105b0ccf84c4e15c900
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

Loading…