2-Methanesulfonylbenzene-1-sulfonyl chloride → HCID 17871262, compound

HRID 1977950Notes

Reaction equation

HRID 1977950 reaction equation
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[CH3:11][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21](Cl)(=[O:23])=[O:22])(=[O:14])=[O:13]>C([O-])(O)=O.[Na+].ClCCl.O>[CH3:8][C:7]1[CH:9]=[C:2]([O:10][S:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[S:12]([CH3:11])(=[O:14])=[O:13])(=[O:23])=[O:22])[CH:3]=[C:4]([OH:5])[CH:6]=1

Participants

6

Reactant 2

HCID 27351782-Methanesulfonylbenzene-1-sulfonyl chlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 17871262HCID 17871262, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of orcinol monohydrate (1.68 g, 12 mmol) and 2-methylsulfonylbenzenesulfonyl chloride (3.0 g, 11.8 mmol) in saturated NaHCO3 (25 mL) and dichloromethane (25 mL) was stirred vigorously at room temperature for one week. The reaction mixture was diluted with 50 mL of water and extracted into dichloromethane (3×50 mL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was treated with dichloromethane and ether to initiate crystallization. The mixture was filtered to provide 1.05 g (26% yield) of a white solid. 1H-NMR (300 MHz, CDCl3) δ2.22 (s, 3H), 3.45 (s, 3H), 5.20 (s, 1H), 6.51 (t, 1H), 6.54 (s, H), 6.61 (s, 1H), 7.74 (td, 1H, J=7.7, 1.4 Hz), 7.87 (td, 1H, J=7.7, 1.3 Hz), 8.12 (dd, 1H, J=7.8, 0.7 Hz), and 8.44 (dd, 1H, J=7.8, 0.5 Hz).

Workup

  1. extractionextracted into dichloromethane (3×50 mL)
  2. washThe organic phase was washed with brine (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvent in vacuo
  5. additionthe residue was treated with dichloromethane and ether
  6. customcrystallization
  7. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-02faaa24642543668ef765884af356a0
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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