Hydrochloric Acid → HCID 23283985, compound

HRID 370340Notes

Reaction equation

HRID 370340 reaction equation
C(N(CC)CC)C.[CH:8]1([C:11]([C:13]2[CH:14]=[N:15][O:16][C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([F:29])([F:28])([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[O:12])[CH2:10][CH2:9]1.Cl>ClCCl>[C:14]([CH:13]([C:11]([CH:8]1[CH2:9][CH2:10]1)=[O:12])[C:17]([C:18]1[CH:19]=[CH:20][C:21]([S:24]([F:27])([F:29])([F:25])([F:26])[F:28])=[CH:22][CH:23]=1)=[O:16])#[N:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 23283987HCID 23283987, compound2×

Product 1

HCID 23283985HCID 23283985, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.73 g) was added to a stirred solution of 4-cyclopropylcarbonyl-5-(4-pentafluorosulphanylphenyl)isoxazole (Compound 2, 0.4 g) in dichloromethane. After 16 hours the solution was washed (2M hydrochloric acid), dried (magnesium sulphate) and evaporated to dryness. The residue was purified by chromatography eluting with ethyl acetate/hexane to give a residue which was suspended in dichloromethane and shaken with hydrochloric acid until dissolved. The organic phase was evaporated and triturated with hexane to give 2-cyano-3-cyclopropyl-1-(4-pentafluorosulphanylphenyl)propan-1,3-dione as a white solid (Compound 3, m.p.108-110° C.

Workup

  1. washAfter 16 hours the solution was washed (2M hydrochloric acid)
  2. dry with materialdried (magnesium sulphate)
  3. customevaporated to dryness
  4. customThe residue was purified by chromatography
  5. washeluting with ethyl acetate/hexane
  6. customto give a residue which
  7. dissolutionuntil dissolved
  8. customThe organic phase was evaporated
  9. customtriturated with hexane

Sources & evidence

ORD record
ord-bd1b472d57f64b2c908a506df96b7121
Source dataset
uspto-grants-2000_10
Patent number
US06140528

Reaction notes

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