Hydrochloric Acid → HCID 21476637, compound

HRID 229201Notes

Reaction equation

HRID 229201 reaction equation
[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(Cl)(=O)C(Cl)=O.[C:20]1([O:26][CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl.CN(C=O)C>[CH3:27][O:26][C:20]1[CH:25]=[CH:24][C:23]([C:9]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:13][CH:12]=2)=[O:11])=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 65578Oxalyl chlorideHCID 77670p-(Methylsulphonyl)benzoic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21476637HCID 21476637, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-(Methylsulfonyl)benzoic acid (0.5 g, 2.42 mmol) was suspended in CH2Cl2 (15 mL). Oxalyl chloride (0.44 mL, 4.85 mmol) was added dropwise, followed by addition of two drops of DMF. The reaction mixture was stirred at room temperature for 3 h. CH2Cl2 and the excess of oxalyl chloride were removed under vacuum. The residue was dissolved in CH2Cl2(10 mL) with anisole (0.54 mL, 4.84 mmol). Cooled in an ice bath, aluminum chloride (0.49 g, 3.63 mmol) was added in portions. The mixture was stirred at 0° C. for 2 h, then heated at reflux overnight. Cooled to room temperature, the mixture was poured into 1 N HCl (15 mL) with ice, the pinkish solid was collected and washed with water, hexanes and dried to give 0.50 g (71%) of the title compound (92) as light pink solid. 1H NMR (400 MHz, DMSO-d6): δ 3.28 (s, 3H), 3.85 (s, 3H), 7.09 (d, J=8.8 Hz, 2H), 7.76 (d, J=8.8 Hz, 2H), 7.88 (d, J=8.3 Hz, 2H), 8.07 (d, J=8.2 Hz, 2H). LCMS (ESI): m/z 291 (M+H)+.

Workup

  1. customCH2Cl2 and the excess of oxalyl chloride were removed under vacuum
  2. temperatureCooled in an ice bath
  3. stirringThe mixture was stirred at 0° C. for 2 h
  4. temperatureheated
  5. temperatureat reflux overnight
  6. temperatureCooled to room temperature
  7. customthe pinkish solid was collected
  8. washwashed with water, hexanes
  9. customdried

Sources & evidence

ORD record
ord-c2aa3f2149f645e1a21be466f1db2b63
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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