Pyridine → HCID 10639752, compound

HRID 1463261Notes

Reaction equation

HRID 1463261 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[S:12][CH:11]=[C:10]([S:13]([NH2:16])(=[O:15])=[O:14])[CH:9]=2)=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].C1COCC1>C(OCC)(=O)C>[C:25]([O:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[S:12][CH:11]=[C:10]([S:13]([NH2:16])(=[O:15])=[O:14])[CH:9]=2)=[O:7])=[CH:4][CH:3]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 10612967HCID 10612967, compound

Product 1

HCID 10639752HCID 10639752, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

58 mg (0.20 mmol) of 5-(4-hydroxybenzoyl)-3-thiophene sulfonamide, 81 mL (1.0 mmol) of pyridine and 94 mL (1.0 mmol) of acetic anhydride were added to 4 mL of THF. The reaction was stirred at rt for 1 1/4 h and then diluted with ethyl acetate. The organic phase was washed with water (2×) followed with brine. The solution was dried over MgSO4 and the solvent removed under vacuum. Flash chromatography utilizing 1:1 hexane/ethyl acetate as the eluant recovered 51 mg of 5-(4-acetoxybenzoyl)-3-thiophene sulfonamide as tan color crystals.

Workup

  1. washThe organic phase was washed with water (2×)
  2. dry with materialThe solution was dried over MgSO4
  3. customthe solvent removed under vacuum
  4. customrecovered 51 mg of 5-(4-acetoxybenzoyl)-3-thiophene sulfonamide as tan color crystals

Sources & evidence

ORD record
ord-53330cff49224dea96d06e6ec130a927
Source dataset
uspto-grants-1994_04
Patent number
US05300499

Reaction notes

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