Dimethylformamide → Methyl 4-chloro-3-(methylsulfonyl)benzoate

HRID 1291702Notes

Reaction equation

HRID 1291702 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-])=[O:7])=[CH:4][C:3]=1[S:11]([OH:13])=[O:12].[Na+].[Na+].Cl[C:17]1C=CC(C([O-])=O)=CC=1S(O)=O.CI.CN(C)[CH:33]=[O:34]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:34][CH3:33])=[O:7])=[CH:4][C:3]=1[S:11]([CH3:17])(=[O:13])=[O:12]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 70253681Disodium bis(4-chloro-3-sulfinobenzoate)

Product 1

HCID 10490815Methyl 4-chloro-3-(methylsulfonyl)benzoate

Conditions

Temperature
60 °C

Procedure

250 g of disodium 4-chloro-3-hydroxysulfinylbenzoate were suspended in 500 ml of abs. dimethylformamide at RT, 218 ml of methyl iodide (3.5 mol) were added and the reaction mixture was heated to 60° C. It was subsequently stirred at this temperature for 4 hours, then allowed to stand at RT overnight. The mixture became solid on cooling. It was warmed to 70° C., diluted with 250 ml of abs. dimethylformamide and subsequently stirred at 70° C. for a further 3 hours. The solvent was distilled off, the residue was taken up in 1000 ml of water, stirred for 30 minutes in an ice bath, filtered off with suction and washed 3 times with about 200 ml of water each time, sucked dry and dried in vacuo (50° C.).

Workup

  1. waitto stand at RT overnight
  2. temperatureon cooling
  3. temperatureIt was warmed to 70° C.
  4. additiondiluted with 250 ml of abs
  5. distillationThe solvent was distilled off
  6. stirringstirred for 30 minutes in an ice bath
  7. filtrationfiltered off with suction
  8. washwashed 3 times with about 200 ml of water each time
  9. customsucked dry
  10. customdried in vacuo (50° C.)

Sources & evidence

ORD record
ord-7d7bd4dd64fc4a6a82ee81d54790a246
Source dataset
uspto-grants-1998_05
Patent number
US05753710

Reaction notes

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