Sodium Carbonate → HCID 58167767, compound

HRID 1690277Notes

Reaction equation

HRID 1690277 reaction equation
O[CH2:2][C:3]([NH:6][C:7](=[O:22])[C:8]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[O:20][CH3:21])([CH3:5])[CH3:4].S(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[CH3:21][O:20][C:9]1[CH:10]=[C:11]([C:16]([F:19])([F:18])[F:17])[CH:12]=[C:13]([O:14][CH3:15])[C:8]=1[C:7]1[O:22][CH2:4][C:3]([CH3:2])([CH3:5])[N:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 58167761HCID 58167761, compound

Product 1

HCID 58167767HCID 58167767, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5.66 g (17.62 mmol) N-(2-hydroxy-1,1-dimethyl-ethyl)-2,6-dimethoxy-4-trifluoromethyl-benzamide in 60 ml dichloromethane was cooled to 10° C. 3.8 ml (52.85 mmol) thionylchloride was added drop-wise. The temperature rose to 15° C. The mixture was stirred at room temperature for 1 hour. The solution was added drop-wise to 130 ml of a cooled 2M sodium carbonate solution. The emulsion was diluted with water and filtered, to remove the white solid. The organic layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude light yellow solid (5.27 g) was purified with flash column chromatography on silica (70 g) eluting with a gradient formed from n-heptane and ethyl acetate (0 to 50%) to provide 4.8 g (yield: 89.8%) of the title compound as a white solid. MS (m/e): 304.2 (M+H+).

Workup

  1. customrose to 15° C
  2. filtrationfiltered
  3. customto remove the white solid
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with dichloromethane
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude light yellow solid (5.27 g) was purified with flash column chromatography on silica (70 g)
  10. washeluting with a gradient
  11. customformed from n-heptane and ethyl acetate (0 to 50%)

Sources & evidence

ORD record
ord-de27cf99c02a49589e245469054e2cf8
Source dataset
uspto-grants-2012_04
Patent number
US08153653B2

Reaction notes

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