Methyl iodide → 6-[4-(3,4-Dichloro-phenylsulfinyl)-butoxy]-1,4,4-trimethyl-4H-3,1-benzoxazin-2-one

HRID 463078Notes

Reaction equation

HRID 463078 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]3[NH:24][C:23](=[O:25])[O:22][C:21]([CH3:27])([CH3:26])[C:20]=3[CH:28]=2)=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:29]I.[OH-].[Na+]>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]3[N:24]([CH3:29])[C:23](=[O:25])[O:22][C:21]([CH3:26])([CH3:27])[C:20]=3[CH:28]=2)=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 132539416-[4-(3,4-Dichloro-phenylsulfinyl)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one

Product 1

HCID 132540206-[4-(3,4-Dichloro-phenylsulfinyl)-butoxy]-1,4,4-trimethyl-4H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.1 gm (0.0025 mol) of 6-[4-(3,4-dichloro-phenylsulfinyl)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 1 ml of methyl iodide in 30 ml of methylene chloride are mixed with 30 ml of 2N sodium hydroxide solution (0.06 mol) and a spatula tip of tetrabutylammonium hydrogen sulfate, and the mixture is stirred for 18 hours at ambient temperature. The organic phase is separated, washed twice with water, and dried with sodium sulfate, and the methylene chloride is distilled off. The residue is purified by column chromatography [silica gel; chloroform/acetone (40:1)]. The uniform fractions are concentrated by evaporation, the residue is stirred with diisopropylether, and the crystal slurry is subjected to suction filtration and dried.

Workup

  1. customThe organic phase is separated
  2. washwashed twice with water
  3. dry with materialdried with sodium sulfate
  4. distillationthe methylene chloride is distilled off
  5. customThe residue is purified by column chromatography [silica gel; chloroform/acetone (40:1)]
  6. concentrationThe uniform fractions are concentrated by evaporation
  7. filtrationthe crystal slurry is subjected to suction filtration
  8. customdried

Sources & evidence

ORD record
ord-f2849dca1ed8412ab98283ff14962e73
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Reaction notes

Loading…