1-Benzofuran-2-sulfonyl chloride → HCID 67971263, compound

HRID 1025266Notes

Reaction equation

HRID 1025266 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)(=[O:12])=[O:11].[O:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH:20]=[C:19]1[S:27](Cl)(=[O:29])=[O:28]>N1C=CC=CC=1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([NH:9][S:10]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:12])=[O:11])=[C:2]([NH:1][S:27]([C:19]2[O:18][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH:20]=2)(=[O:28])=[O:29])[CH:7]=1

Participants

4

Reactant 2

HCID 27951721-Benzofuran-2-sulfonyl chloride2×HCID 16776759HCID 16776759, compound

Product 1

HCID 67971263HCID 67971263, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-(2-amino-4-chlorophenyl)thiophene-2-sulfonamide (CAS RN: 926205-90-5) (140 mg, ˜0.47 mmol) in pyridine (2.5 ml) was added benzofuran-2-sulfonyl chloride (102 mg, 0.47 mmol) and the mixture was stirred at room temperature for 16 h. More benzofuran-2-sulfonyl chloride (51 mg, 0.24 mmol) was added and the reaction was stirred for another 24 h, concentrated in vacuo to remove most of solvent. The residual thick syrup was quenched with 6M HCl and diluted with H2O. The resulting suspension was filtered and washed with H2O (×3). The crude product was purified by flash column chromatography on silica gel (25-50% EtOAc-hexane) to yield 43 mg of product slightly contaminated with impurities. This material was triturated with CH2Cl2 to form a sandy colored solid, which was filtered and rinsed with minimal amount of CH2Cl2 to yield 23 mg (10%) of Compound 24.

Workup

  1. stirringthe reaction was stirred for another 24 h
  2. concentrationconcentrated in vacuo
  3. customto remove most of solvent
  4. customThe residual thick syrup was quenched with 6M HCl
  5. additiondiluted with H2O
  6. filtrationThe resulting suspension was filtered
  7. washwashed with H2O (×3)
  8. customThe crude product was purified by flash column chromatography on silica gel (25-50% EtOAc-hexane)

Sources & evidence

ORD record
ord-c483abc9dfca4f15810d22864260c985
Source dataset
uspto-grants-2014_05
Patent number
US08729066B2

Reaction notes

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