Water → HCID 86732539, compound

HRID 623306Notes

Reaction equation

HRID 623306 reaction equation
[Cl:1][C:2]1[C:3]([CH2:12][CH:13]=[N:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.S(=O)(=O)(O)O.Cl[CH2:33]Cl.[OH2:35]>CO>[Cl:1][C:2]1[C:3]([CH2:12][CH:13]([NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:23])([F:24])[F:25])[O:35][CH3:33])=[N:4][CH:5]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 86732538HCID 86732538, compound

Product 1

HCID 86732539HCID 86732539, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.16 g of N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethylidene}-2-(trifluoromethyl)benzamide (Int-6) were diluted in 2 mL of methanol. 50 μL of sulfuric acid 99% were added. The reaction mixture was stirred at room temperature for 48 hours. A mixture of dichloromethane (10 mL) and water (5 mL) was added. After separation, the aqueous phase was extracted twice with dichloromethane. The combined organic phases were washed with 5 mL of water, dried over magnesium sulfate, filtered, concentrated to yield to 0.150 g of crude material, which was purified by chromatography on silica gel to yield 0.107 g (63%) of desired product N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1-methoxyethyl}-2-(trifluoromethyl)benzamide (Ia-111), [M+1]=427.

Workup

  1. additionwas added
  2. customAfter separation
  3. extractionthe aqueous phase was extracted twice with dichloromethane
  4. washThe combined organic phases were washed with 5 mL of water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield to 0.150 g of crude material, which
  9. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9b6368c4f43e4419ae61e9ff6c473a4f
Source dataset
uspto-grants-2016_04
Patent number
US09301526B2

Reaction notes

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