Acetone → HCID 22912940, compound

HRID 1378736Notes

Reaction equation

HRID 1378736 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[Cl:14][C:15]1[C:20]([NH:21][C:22]([CH3:26])([CH3:25])[CH2:23][OH:24])=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=[CH:17][CH:16]=1.CC(C)=O>C(O)(C)C>[Cl:14][C:15]1[C:20]([NH:21][C:22]([CH3:26])([C:23]([OH:3])=[O:24])[CH3:25])=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 22912813HCID 22912813, compoundHCID 131709961Jones' reagent

Product 1

HCID 22912940HCID 22912940, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Jones reagent (2.67M) is added in aliquots (30 ml, 15 ml, 10 ml, 5 ml) every 15 min to a solution of 2-[N-(6-Chloro-2-nitrophenyl)]amino-2-methyl-1-propanol (IX, EXAMPLE 13, 21.6 g) and acetone (1.65 l) at 0° until the reaction is done as measured by TLC analysis. After 1 hr total time, isopropanol (90 ml) is added and the mixture is allowed to warm to 20°-25°. The mixture is filtered and the solids washed with acetone several times. The combined filtrates are concentrated and partitioned between ether (1.0 l) and potassium hydroxide (10%, 3×100 ml). The basic layer is acidified (3N hydrochloric acid) and extracted with methylene chloride (3×200 ml). The methylene chloride phase is dried over magnesium sulfate, filtered, and concentrated to give the title compound sufficient pure to be used in the next step without additional purification, mp 107°-109°; IR (mineral oil) 3358, 2953, 2924, 1715, 1597, 1496, 1330, 1280, 1231, 1174, 1105 and 747 cm-1 ; NMR (CDCl3) 8.00, 7.61, 7.06, 6.5-7.1 and 1.54 δ; MS (m/z) 258 and 213.

Workup

  1. temperatureto warm to 20°-25°
  2. filtrationThe mixture is filtered
  3. washthe solids washed with acetone several times
  4. concentrationThe combined filtrates are concentrated
  5. custompartitioned between ether (1.0 l) and potassium hydroxide (10%, 3×100 ml)
  6. extractionextracted with methylene chloride (3×200 ml)
  7. dry with materialThe methylene chloride phase is dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5412721217b64ab39b8cb4e028a4a8ac
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

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