Acetic Acid → HCID 18314476, compound

HRID 1274591Notes

Reaction equation

HRID 1274591 reaction equation
[CH3:1][C:2]([CH3:20])([C:8]1[C:12]2[CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(O)(=O)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(Cl)Cl.[Fe]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]2[S:10][N:9]=[C:8]([C:2]([CH3:20])([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:12]=2[CH:13]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl Acetate2×HCID 516892Sodium BicarbonateHCID 18314471HCID 18314471, compound

Product 1

HCID 18314476HCID 18314476, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
56 °C

Procedure

A mixture of ethyl α,α-dimethyl-5-nitro-1,2-benzisothiazole-3-acetate (0.714 g, 2.42 mmol), iron powder (0.500 g), 10% acetic acid (23.0 mL) and ethyl acetate (23.0 mL) is stirred at 54-58° C. for one hour, cooled, and poured into saturated sodium hydrogen carbonate solution. The resultant aqueous mixture is extracted with ethyl acetate. The combined organic extracts are washed sequentially with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a yellow oil. Column chromatography of the oil using silica gel and a 10% ethyl acetate in methylene chloride solution gives the title product as a light brown oil which is identified by NMR spectral analysis.

Workup

  1. temperaturecooled
  2. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  3. washThe combined organic extracts are washed sequentially with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a yellow oil

Sources & evidence

ORD record
ord-05df56dcc04a461fbd5d54bf68ea1576
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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