Ethyl Acetate → HCID 22266217, compound

HRID 489647Notes

Reaction equation

HRID 489647 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH2:13])=[CH:3][CH:2]=1.[CH3:14][S:15](Cl)(=[O:17])=[O:16].N.CO.CCOC(C)=O>ClCCCl.CCCCCC>[CH3:14][S:15]([NH:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)(=[O:17])=[O:16]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 135464462-(Pyridin-4-yl)anilineHCID 21705897Ammonia methanol

Product 1

HCID 22266217HCID 22266217, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-(4-pyridyl)phenylamine (Step b) (500 mg, 2.9 mmol) in 1,2-dichloroethane (35 mL) was stirred magnetically under N2 in a 100 mL round-bottomed flask at 25° C. The solution was treated with TEA (Aldrich) (400 μL, 2.9 mmol) followed by methanesulfonyl chloride (Aldrich) (230 μL, 335 mg, 2.9 mmol). The vessel was heated in a 50° C. oil bath for 3 h. The reaction mixture was concentrated in vacuo and the resulting residue was partitioned between EtOAc (100 mL) and satd NaHCO3 (50 mL). The organic layer was washed with satd NaCl (50 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford a yellow oil. To the oil was added 5:25:75 1 M NH3/MeOH:EtOAc:hexane (10 mL). A yellow precipitate formed which was collected by filtration and dried in vacuo at 40° C. to afford the title compound as a yellow solid (480 mg). MS (ESI, pos. ion) m/z: 249 (M+1); (ESI, neg. ion) m/z: 247 (M−1). Calc'd for C12H12N2O2S: 248.30.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting residue was partitioned between EtOAc (100 mL) and satd NaHCO3 (50 mL)
  3. washThe organic layer was washed with satd NaCl (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow oil
  8. customA yellow precipitate formed which
  9. filtrationwas collected by filtration
  10. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-d5558f1c63a04c2ea3ce44d528b3a819
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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