Hydrochloric Acid → HCID 12421467, compound

HRID 1816242Notes

Reaction equation

HRID 1816242 reaction equation
[CH3:1][S:2]([CH3:5])(=[O:4])=[O:3].[H-].[Na+].[C:8](OC)(=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH2:11].Cl>CS(C)=O>[NH2:11][C:10]1[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=1[C:8](=[O:16])[CH2:1][S:2]([CH3:5])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6213Dimethyl SulfoneHCID 8635Methyl AnthranilateHCID 24758Sodium hydride

Product 1

HCID 12421467HCID 12421467, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

Dimethylsulfone (120 g, 1.28 mol) was stirred in DMSO (350 mL). Sodium hydride (48 g of 60 wt % in mineral oil) was added in portions and the mixture heated to 60° C. Methyl anthranilate (48.3 g, 0.32 mol) was added dropwise over 3 hours while the temperature rose to 100° C. The mixture was poured into ice (500 mL) and concentrated HCl (100 mL) and the mixture stored at 4° C. overnight. The mixture was extracted with dichloromethane (3×400 mL), and the combined extracts were washed with saturated bicarbonate (3×30 mL), dried (MgSO4), and reduced to 800 mL volume. The solid that formed was removed by filtration. The filtrate was reduced to 80 mL volume. The resulting solid was collected and washed with a small volume of dichloromethane. The solid was recrystallized from chloroform to give 1-(2-aminophenyl)-2-(methylsulfonyl)ethanone (24 g).

Workup

  1. customrose to 100° C
  2. extractionThe mixture was extracted with dichloromethane (3×400 mL)
  3. washthe combined extracts were washed with saturated bicarbonate (3×30 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solid that formed
  6. customwas removed by filtration
  7. customThe resulting solid was collected
  8. washwashed with a small volume of dichloromethane
  9. customThe solid was recrystallized from chloroform

Sources & evidence

ORD record
ord-b3ef8a12a2b84ea0a41df9852d0b0a85
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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