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

HRID 442989Notes

Reaction equation

HRID 442989 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 aqueous 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 of a white solid. 1H-NMR (300 MHz, CDCl3) δ 2.22 (s, 3H), 3.45 (s, 3H), 5.20 (s, 1H), 6.51 (t, 1H), 6.54 (s, 1H), 6.61 (s, 1H), 7.74 (td, 1H, J=1.4, 7.7 Hz), 7.87 (td, 1H, J=1.3, 7.7 Hz), 8.12 (dd, 1H, J=0.66, 7.8 Hz), and 8.44 (dd, 1H, J 0.52, 7.8 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-7e3cea2af3b24a04b90f553393a9742d
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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