Benzenesulfonyl chloride → HCID 57920397, compound

HRID 1691545Notes

Reaction equation

HRID 1691545 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[S:12]1[C:16]([NH2:17])=[CH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]1=2>N1C=CC=CC=1>[S:12]1[C:16]([NH:17][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[CH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]1=2

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 66906726Benzo[b]thiophen-2-amine hydrochloride

Product 1

HCID 57920397HCID 57920397, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzenesulfonyl chloride (0.661 mL, 5.15 mmol) was added to a solution of compound 1-C (0.87 g, 4.69 mmol) in pyridine (10 mL) at 0° C. The ice bath was removed and the solution was stirred at ambient temperature for 2 h. The solvent was evaporated in vacuo, and the residue was partitioned between 2 N HCl and dichloromethane. The organic layer was dried over magnesium sulfate and the solvent evaporated in vacuo. The residue was pre-absorbed on silica gel and purified by flash column chromatography, eluting with a gradient of ethyl acetate (10-50%) in heptane, to afford compound 1-D as a colorless solid (1.19 g, 88%). 1H-NMR (CDCl3): δ 6.96 (s, 1H), 7.25-7.34 (m, 2H), 7.44-7.49 (m, 2H), 7.55-7.66 (m, 3H), 7.84-7.88 (m, 2H); MS: m/z 290.1 (MH+).

Workup

  1. customThe ice bath was removed
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was partitioned between 2 N HCl and dichloromethane
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent evaporated in vacuo
  6. customThe residue was pre-absorbed on silica gel
  7. custompurified by flash column chromatography
  8. washeluting with a gradient of ethyl acetate (10-50%) in heptane
  9. customto afford compound 1-D as a colorless solid (1.19 g, 88%)

Sources & evidence

ORD record
ord-17e19fa8c829490b911a56458ca7ef67
Source dataset
uspto-grants-2012_04
Patent number
US08153682B2

Reaction notes

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