Thionyl Chloride → HCID 66742926, compound

HRID 449577Notes

Reaction equation

HRID 449577 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[C:3]=1[C:4]([NH:6][C:7]([CH3:11])([CH3:10])[CH2:8][OH:9])=O.S(Cl)(Cl)=O>ClCCl>[CH3:10][C:7]1([CH3:11])[CH2:8][O:9][C:4]([C:3]2[C:2]([F:1])=[CH:15][C:14]([F:16])=[CH:13][C:12]=2[F:17])=[N:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 65100569HCID 65100569, compound

Product 1

HCID 66742926HCID 66742926, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4,6-trifluoro-N-(2-hydroxy-1,1-dimethyl-ethyl)-benzamide (43.8 g, 177.1 mmol) in dry dichloromethane (400 mL) was added thionyl chloride (58.9 ml, 415 mmol) via slow drop-wise addition over 25 minutes (reaction flask was immersed in an ice bath part way through the addition to control the temperature). After complete addition the material was stirred at ambient temperature over night. The volume was reduced to 30% by concentration under vacuum. To that was added ether (200 ml) and a solid precipitate (39.94 g off-white solid) was collected by filtration. The ether filtrate was set aside and the solid material was taken up in water (120 ml) and treated with an aqueous solution of sodium hydroxide (2N, 55 ml). Ethyl acetate (120 ml) was added and the mixture was transferred to a separatory funnel and shaken. The organic phase was collected and washed with an equal volume of water. The ethyl acetate phase was collected and the aqueous phases were back extracted with ethyl acetate (2×100 ml). The combined organic phases were dried (magnesium sulfate), filtered and concentrated in vacuo to provide the desired as a pure off-white solid (33.98 g). (M+H)+=230 m/e.

Workup

  1. additionvia slow drop-wise addition over 25 minutes (
  2. customreaction flask
  3. customwas immersed in an ice bath
  4. additionpart way through the addition
  5. additionAfter complete addition the material
  6. concentrationThe volume was reduced to 30% by concentration under vacuum
  7. additionTo that was added ether (200 ml)
  8. filtrationa solid precipitate (39.94 g off-white solid) was collected by filtration
  9. additiontreated with an aqueous solution of sodium hydroxide (2N, 55 ml)
  10. additionEthyl acetate (120 ml) was added
  11. customthe mixture was transferred to a separatory funnel
  12. stirringshaken
  13. customThe organic phase was collected
  14. washwashed with an equal volume of water
  15. customThe ethyl acetate phase was collected
  16. extractionthe aqueous phases were back extracted with ethyl acetate (2×100 ml)
  17. dry with materialThe combined organic phases were dried (magnesium sulfate)
  18. filtrationfiltered
  19. concentrationconcentrated in vacuo
  20. customto provide the

Sources & evidence

ORD record
ord-0c56728d428c49f0ab48cb0db478b6fc
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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