Triethylamine → 2-Acetyl-7-methoxy-N-[3-pyridylmethyl]-4-benzofuransulphonamide

HRID 965171Notes

Reaction equation

HRID 965171 reaction equation
C(N(CC)CC)C.[C:8]([C:11]1[O:12][C:13]2[C:14](=[C:16]([S:22](Cl)(=[O:24])=[O:23])[CH:17]=[CH:18][C:19]=2[O:20][CH3:21])[CH:15]=1)(=[O:10])[CH3:9].[NH2:26][CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1>ClCCl>[C:8]([C:11]1[O:12][C:13]2[C:14](=[C:16]([S:22]([NH:26][CH2:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)(=[O:24])=[O:23])[CH:17]=[CH:18][C:19]=2[O:20][CH3:21])[CH:15]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 310183-PyridinemethanamineHCID 138514332-Acetyl-7-methoxy-4-benzofuransulphonyl chloride

Product 1

HCID 190759662-Acetyl-7-methoxy-N-[3-pyridylmethyl]-4-benzofuransulphonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.43 ml) was added to a solution of 2-acetyl-7-methoxy-4-benzofuransulphonyl chloride (600 mg) and 3-(aminomethyl)pyridine (0.25 ml) in dichloromethane at room temperature. The resultant mixture was stirred for 20 hours and then diluted with dichloromethane (20 ml). The solution was washed with water (20 ml) and brine (20 ml) and dried (MgSO4). Concentration in vacuo provided a dark oil which was applied to a silica column and eluted with 2% methanol in dichloromethane. The title compound was obtained as a pale yellow solid (161 mg). Mp 168°-170° C.

Workup

  1. washThe solution was washed with water (20 ml) and brine (20 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationConcentration in vacuo
  4. customprovided a dark oil which
  5. washeluted with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-f9116923a9c04a33ba82d4bf0aa16ade
Source dataset
uspto-grants-1998_06
Patent number
US05773467

Reaction notes

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