Methanol → HCID 44391097, compound

HRID 1180659Notes

Reaction equation

HRID 1180659 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Cl:14][C:15]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18].C(Cl)(Cl)Cl.CO>C(Cl)Cl.N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[Cl:14][C:15]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:16]=1[C:17]([NH:13][S:10]([C:7]1[CH:8]=[CH:9][C:4]2[CH:3]=[CH:2][O:1][C:5]=2[CH:6]=1)(=[O:11])=[O:12])=[O:18]

Participants

8

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 666452,4-Dichlorobenzoyl chlorideHCID 198073291-Benzofuran-6-sulfonamide

Product 1

HCID 44391097HCID 44391097, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of benzofuran-6-sulfonamide (120 mg, 0.608 mmol) in CH2Cl2 (3.6 mL) and pyridine (2.3 mL) is added DMAP (75 mg, 0.611 mmol) and 2,4-dichlorobenzoyl chloride (153 mg, 0.730 mmol) and the reaction is stirred at room temperature overnight. The reaction mixture is diluted with CH2Cl2 then washed with 2 M HCl (2×) and dried (MgSO4). The organic solution is filtered and evaporated under vacuum to give the crude product. Flash chromatography on silica gel eluting with a gradient {CH2Cl2to CH2Cl2:(CHCl3:MeOH) [4:1(9:1)]} gives the title compound as a tan solid. ES(−)MS m/z 368, (M−H)− consistent with 2 Cl.

Workup

  1. washthen washed with 2 M HCl (2×)
  2. dry with materialdried (MgSO4)
  3. filtrationThe organic solution is filtered
  4. customevaporated under vacuum
  5. customto give the crude product

Sources & evidence

ORD record
ord-96b4729fdf1844b09405ffc7025ddf02
Source dataset
uspto-grants-2007_10
Patent number
US07282595B2

Reaction notes

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