2-Methoxybenzenesulfonyl Chloride → HCID 67417832, compound

HRID 1429352Notes

Reaction equation

HRID 1429352 reaction equation
[NH2:1][CH:2]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30](Cl)(=[O:32])=[O:31]>N1C=CC=CC=1>[O:14]=[C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12](=[O:13])[N:4]1[CH2:3][CH:2]([NH:1][S:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[O:23][CH3:22])(=[O:32])=[O:31])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 37458512-Methoxybenzenesulfonyl ChlorideHCID 67382647HCID 67382647, compound

Product 1

HCID 67417832HCID 67417832, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of compound 2b (800 mg, 2.8 mmol) in pyridine (20 mL) was added 2-methoxybenzene-1-sulfonyl chloride (942 mg, 4.5 mmol) at 10° C. The mixture was stirred at rt overnight and then concentrated in vacuo. The residue was dissolved in DCM (20 mL), washed with water (20 mL) and brine (20 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash chromatography (PE:EA=2:1) to give compound 2c as a white solid (1.13 g, 83% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in DCM (20 mL)
  3. washwashed with water (20 mL) and brine (20 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel flash chromatography (PE:EA=2:1)

Sources & evidence

ORD record
ord-5837764da1524b61a6a04cf305f14b36
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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