Acetone → HCID 67429523, compound

HRID 1423960Notes

Reaction equation

HRID 1423960 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([SH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:12][C:13]([CH3:15])=O.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:13]([CH3:15])([CH3:12])[O:8][C:7](=[O:9])[C:6]=2[CH:10]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 155577875-Chloro-2-sulfanylbenzoic acid

Product 1

HCID 67429523HCID 67429523, compoundYield 25.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-chloro-2-mercapto-benzoic acid (2.5 g, 13.25 mmol) (commercial available from Biogene Organics), acetone (7.9 g, 136 mmol), (+/−) camphor sulfonic acid (1.54 g, 6.63 mmol) and 4 A moleculare sieves (1.5 g) in CHCl3 was heated to refulx for 3 days. Reaction mixture was diluted with CH2Cl2 (100 mL) and then washed with saturated NaHCO3 aqueous solution (2×50 mL). Organic layer was washed with brine, dried over MgSO4, filtered and concentrated. Crude residue was passed through a pad of silica gel and eluted with CH2Cl2. Filtrate was concentrated to provide the title compound (769 mg). 1H NMR (200 MHz, CDCl3): δ (ppm)=8.15 (d, J=2.4 Hz, 1H), 7.44 (dd, J=8.3, 2.0 Hz, 1H), 7.21 (d, J=8.3 Hz, 1H), 1.83 (s, 6H).

Workup

  1. temperaturewas heated
  2. customReaction mixture
  3. washwashed with saturated NaHCO3 aqueous solution (2×50 mL)
  4. washOrganic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washeluted with CH2Cl2
  9. concentrationFiltrate was concentrated

Sources & evidence

ORD record
ord-07e6be3d4c43456fbc3eb6b4d0a86e59
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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