Sulfolane → HCID 69831923, compound

HRID 369611Notes

Reaction equation

HRID 369611 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[C:14]3[CH:15]=[C:16]([N+:20]([O-:22])=[O:21])[C:17](Cl)=[CH:18][C:13]=3[S:12][N:11]=2)=[CH:5][CH:4]=1.[F-:23].[K+].S1(CCCC1)(=O)=O>>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[C:14]3[CH:15]=[C:16]([N+:20]([O-:22])=[O:21])[C:17]([F:23])=[CH:18][C:13]=3[S:12][N:11]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 31347SulfolaneHCID 522689Potassium FluorideHCID 69831429HCID 69831429, compound

Product 1

HCID 69831923HCID 69831923, compoundYield 30.1%

Conditions

Temperature
154 °C

Procedure

A mixture of 3-(6-methoxy-m-tolyl)-6-chloro-5-nitro-1,2-benzisothiazole (7.30 g, 0.0218 mol), potassium fluoride (6.33 g, 0.109 mol) 18-crown-6 (2.31 g, 0.0872 mol) and sulfolane is stirred 19 hours at 154° C., cooled to room temperature, and poured into ice water. The resultant solid is filtered and chromatographed on silica gel with methylene chloride to afford a solid which is recrystallized from acetonitrile to afford a tan powder. The powder is recrystallized from ethyl acetate to give the title compound as a tan solid (2.09 g, 29.9%) which is identified by NMR spectral analysis.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resultant solid is filtered
  3. customchromatographed on silica gel with methylene chloride
  4. customto afford a solid which
  5. customis recrystallized from acetonitrile
  6. customto afford a tan powder
  7. customThe powder is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5bb4cd73301a4fbba0e62cad1a1db8b9
Source dataset
uspto-grants-2000_10
Patent number
US06140270

Reaction notes

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