Hydrochloric Acid → 1-(2-Aminophenyl)-2-(methylsulfinyl)ethanone

HRID 275317Notes

Reaction equation

HRID 275317 reaction equation
[C:1]([O:10]CC)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[H-].[Na+].[CH3:15][S:16]([CH3:18])=[O:17].Cl>C1C=CC=CC=1.CO.CCOC(C)=O>[NH2:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1](=[O:10])[CH2:15][S:16]([CH3:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 6877Ethyl 2-aminobenzoate2×HCID 24758Sodium hydride

Product 1

HCID 143584271-(2-Aminophenyl)-2-(methylsulfinyl)ethanoneYield 59%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 21584119Ethylacetate methanolSolvent2×

Conditions

Temperature
80 °C

Procedure

From ethyl anthranilate: A mixture of sodium hydride (60% dispersion in mineral oil, 24.00 g, 0.6 mole, 3 equiv.), dry DMSO (71.0 ml, 1.0 mole, 5 equiv.), and benzene (130 ml) was heated at 80° C. until gas evolution ceased (1.5 hr), then was cooled in ice/H2O. A solution of ethyl anthranilate (29.6 ml, 0.2 mole, 1 equiv.) in benzene (100 ml) was added at a rate such that the internal temperature did not exceed 25° C., and the mixture was stirred for 0.5 hr The reaction was poured into ice/H2O and the pH was adjusted to 5-6 with concentrated HCl. EtOAc extraction, drying (MgSO4) and concentration gave a cloudy, orange oil. Silica gel chromatography (3% MeOH/EtOAc, then 5% MeOH/EtOAc) gave 1-(2-aminophenyl)-2-(methylsulfinyl)ethanone (23.43 g, 59%) as a yellow solid. Material prepared in this way was identical to that prepared from isatoic anhydride.

Workup

  1. custom(1.5 hr)
  2. customdid not exceed 25° C.
  3. extractionEtOAc extraction
  4. customdrying
  5. concentration(MgSO4) and concentration
  6. customgave a cloudy, orange oil

Sources & evidence

ORD record
ord-6b654ff40c4a4bc8b33334d852f715d3
Source dataset
uspto-grants-1995_02
Patent number
US05393756

Reaction notes

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