Acetic Anhydride → HCID 47269197, compound

HRID 410476Notes

Reaction equation

HRID 410476 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:14](OC(=O)C)(=[O:16])[CH3:15]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14](=[O:16])[CH3:15])(=[O:11])=[O:12])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 740654-Acetylbenzenesulphonamide

Product 1

HCID 47269197HCID 47269197, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 4-acetylbenzenesulfonamide (0.726 g, 3.64 mmol), acetic anhydride (0.7 ml, 7.42 mmol) and DMAP (22.26 mg, 0.182 mmol) in pyridine (0.7 ml) was stirred at room temperature 16 hrs. The volatiles were removed under reduced pressure, the residue was taken up in toluene (5 mL) and concentrated again (3×). The residue was dissolved in EtOAc (20 mL), washed with brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The solid residue was triturated in Et2O and filtered to give N-[(4-acetylphenyl)sulfonyl]acetamide (670 mg, 2.78 mmol, 76% yield) as a pale yellow solid. MS ESI: [M+Na]+ m/z 264.0. 1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.13 (d, J=9.9, 2H), 8.01 (d, J=9.9, 2H), 2.62 (s, 3H), 1.91 (s, 3H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. concentrationconcentrated again (3×)
  3. dissolutionThe residue was dissolved in EtOAc (20 mL)
  4. washwashed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe solid residue was triturated in Et2O
  9. filtrationfiltered

Sources & evidence

ORD record
ord-605fc08cc36349afa9bbae8e824d4e44
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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