Sodium Hydroxide → HCID 11436092, compound

HRID 913767Notes

Reaction equation

HRID 913767 reaction equation
[CH2:1]([NH:4][C:5](=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)[C:2]#[CH:3].[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:3][C:2]1[O:16][C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:14])([F:15])[F:13])[CH:7]=2)=[N:4][CH:1]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11345177HCID 11345177, compound

Product 1

HCID 11436092HCID 11436092, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
110 °C

Procedure

N-2-Propyn-1-yl-3-(trifluoromethyl)benzamide (Example 370A) (7.0 g, 30.8 mmol) was suspended in sulfuric acid (95˜98%, 15 mL). The mixture was heated at 110° C. for 15 min. After cooling down, ice was added and solution was neutralized with 5N NaOH to pH 7 at 0° C. The mixture was extracted with Et2O three times and the combined organic layers were washed with brine once and dried over MgSO4. Concentration and purification by radial chromatography (0-20% EtOAc-hexanes gradient) afforded the title compound (6.8 g, 97% yield): MS (ES) m/z 228 (M+1).

Workup

  1. temperatureAfter cooling down
  2. additionice was added
  3. extractionThe mixture was extracted with Et2O three times
  4. washthe combined organic layers were washed with brine once
  5. dry with materialdried over MgSO4
  6. concentrationConcentration and purification by radial chromatography (0-20% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-d2b5fd1c3cf3483ab9a6c9f195468488
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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