Dimethylamine → HCID 13688927, compound

HRID 542749Notes

Reaction equation

HRID 542749 reaction equation
[C:1]([O:4][CH2:5][CH:6]1[CH2:10][C:9]2[CH:11]=[CH:12][C:13]([Cl:16])=[C:14]([Cl:15])[C:8]=2[O:7]1)(=[O:3])[CH3:2].Cl[S:18]([OH:21])(=O)=[O:19].O.[CH3:23][NH:24][CH3:25]>S(Cl)(Cl)=O.CCOCC.ClCCl.C(O)C>[C:1]([O:4][CH2:5][CH:6]1[CH2:10][C:9]2[CH:11]=[C:12]([S:18](=[O:21])(=[O:19])[N:24]([CH3:25])[CH3:23])[C:13]([Cl:16])=[C:14]([Cl:15])[C:8]=2[O:7]1)(=[O:3])[CH3:2]

Participants

9

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 24638Chlorosulfonic acidHCID 13861059HCID 13861059, compound

Product 1

HCID 13688927HCID 13688927, compoundYield 88%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

To a solution of 1 g of the oily 2-acetoxymethyl-6,7-dichloro-2,3-dihydrobenzofuran in 2 ml of thionyl chloride is added 1.25 ml of chlorosulfonic acid under ice-cooling and then stirred at room temperature for 2 hours. The reaction mixture is poured into iced water (about 50 g) and extracted with ether. The ether layer is washed water, then dried over calcium chloride, and evaporated to dryness under reduced pressure. To a solution of thus obtained oily product dissolved in 10 ml of dichloromethane is dropwise added 30% ethanol solution of dimethylamine (3.83×3 mmol) at -30° C., and the mixture is stirred for 2 hours. After the addition of dichloromethane, the reaction mixture is washed 10% hydrochloride. The dichloromethane layer is dried and then evaporated under reduced pressure to give an oily product, which is treated with ether to give the objective 2-acetoxymethyl-6,7-dichloro-5-(N,N-dimethylsulfamoyl)-2,3-dihydrobenzofuran (I h-70), yield 88%, m.p. 159°-160° C.

Workup

  1. temperaturecooling
  2. extractionextracted with ether
  3. washThe ether layer is washed water
  4. dry with materialdried over calcium chloride
  5. customevaporated to dryness under reduced pressure
  6. dissolutionTo a solution of thus obtained oily product dissolved in 10 ml of dichloromethane
  7. customat -30° C.
  8. stirringthe mixture is stirred for 2 hours
  9. washthe reaction mixture is washed 10% hydrochloride
  10. dry with materialThe dichloromethane layer is dried
  11. customevaporated under reduced pressure
  12. customto give an oily product, which

Sources & evidence

ORD record
ord-91e15b2bd20540768409b447a091a854
Source dataset
uspto-grants-1987_04
Patent number
US04659709

Reaction notes

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