2-Propanesulfonyl chloride → HCID 74079905, compound

HRID 252309Notes

Reaction equation

HRID 252309 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH3:12])[C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.[CH3:13][CH:14]([S:16](Cl)(=[O:18])=[O:17])[CH3:15]>N1C=CC=CC=1.CCOCC>[CH:14]([S:16]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:12])[C:9]([NH2:11])=[O:10])=[CH:6][CH:7]=1)(=[O:18])=[O:17])([CH3:15])[CH3:13]

Participants

5

Reactant 2

HCID 824082-Propanesulfonyl chlorideHCID 66860046HCID 66860046, compound

Product 1

HCID 74079905HCID 74079905, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

(2R)-2-(4-Aminophenyl)propanamide (0.5 g, 3.05 mmol) was dissolved in pyridine (2 mL) and 2-propanesulfonyl chloride (0.53 mL, 3.66 mmol) was added. The resulting solution was refluxed for 4 h and left overnight at room temperature. After the complete disappearance of the starting amide, the solution was diluted with Et2O (10 mL) and the organic layer washed with 1N HCl (2×5 mL), with H2O (2×5 mL), dried over Na2SO4, filtered and evaporated under vacuum to give (2R)-2-{(4-[(isopropylsulfonyl)amino]phenyl}propanamide as pale yellow solid (667 mg, 2.47 mmol). Yield 81%. mp 125-127° C.; [α]D25 (c=0.3, CH3OH): −12.7°; 1H-NMR (DMSO-d6) δ 9.65 (bs, 1H, SO2NH), 7.40 (bs, 1H, CONH2), 7.25 (d, 2H, J=7 Hz), 7.12 (d, 2H, J=7 Hz), 6.80 (bs, 1H, CONH2), 3.52 (q, 1H, J=7 Hz), 3.15 (m, 1H), 1.22 (d, 3H, J=7 Hz), 1.18 (d, 6H, J=7 Hz).

Workup

  1. temperatureThe resulting solution was refluxed for 4 h
  2. washthe organic layer washed with 1N HCl (2×5 mL), with H2O (2×5 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-1f05a93a931c4ce9a753dafb70fcde55
Source dataset
uspto-grants-2011_01
Patent number
US07868046B2

Reaction notes

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