Dimethylformamide → Methyl 2-(chlorosulfonyl)-4-methoxybenzoate

HRID 1249462Notes

Reaction equation

HRID 1249462 reaction equation
S(Cl)([Cl:3])=O.CO[C:7]1[CH:12]=[CH:11][C:10]([S:13]([O-:16])(=[O:15])=O)=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:8]=1.[Na+].CN(C)[CH:24]=[O:25]>>[Cl:3][S:13]([C:10]1[CH:11]=[C:12]([O:25][CH3:24])[CH:7]=[CH:8][C:9]=1[C:17]([O:19][CH3:20])=[O:18])(=[O:15])=[O:16]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 23672128Sodium 4-methoxy-2-(methoxycarbonyl)benzenesulfonate

Product 1

HCID 13769571Methyl 2-(chlorosulfonyl)-4-methoxybenzoate

Procedure

To 500 ml of thionyl chloride was added portionwise over 1 hour 100 g of the compound of Example 3. The reaction mixture was stirred 0.5 hours, and 5 ml of dimethylformamide was added over 1 hour. The mixture was refluxed overnight. The orange solution was cooled to ambient temperature and concentrated in vacuo to a yellow semisolid. The reaction product was dissolved in 250 ml dichloromethane, and the solution was concentrated in vacuo. The resulting solid was partitioned between ether and water. The organic phase was washed with water, twice with aqeous sodium bicarbonate, dried over magnesium sulfate. Evaporation of the solvent in vacuo gave 47 g of the title compound, m.p. 69°-72° C.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationconcentrated in vacuo to a yellow semisolid
  3. dissolutionThe reaction product was dissolved in 250 ml dichloromethane
  4. concentrationthe solution was concentrated in vacuo
  5. customThe resulting solid was partitioned between ether and water
  6. washThe organic phase was washed with water, twice with aqeous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-8b1c72cfb9e3431d99dbe599fdc45244
Source dataset
uspto-grants-1986_12
Patent number
US04632693

Reaction notes

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