Sulfuryl chloride → 6-[4-(3,4-Dichloro-phenylsulfinyl)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one

HRID 463076Notes

Reaction equation

HRID 463076 reaction equation
S(Cl)(Cl)(=O)=[O:2].[Cl:6][C:7]1[CH:8]=[C:9]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]3[NH:28][C:27](=[O:29])[O:26][C:25]([CH3:31])([CH3:30])[C:24]=3[CH:32]=2)[CH:10]=[CH:11][C:12]=1[Cl:13]>C(Cl)Cl>[Cl:6][C:7]1[CH:8]=[C:9]([S:14]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]3[NH:28][C:27](=[O:29])[O:26][C:25]([CH3:30])([CH3:31])[C:24]=3[CH:32]=2)=[O:2])[CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 132540186-[4-(3,4-dichloro-phenylmercapto)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one

Product 1

HCID 132539416-[4-(3,4-Dichloro-phenylsulfinyl)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1 gm (0.0085 mol) of sulfurylchloride in 5 ml of methylene chloride is added dropwise, at -70° C., to a solution of 3.2 gm (0.0075 mol) of 6-[4-(3,4-dichloro-phenylmercapto)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one in 50 ml of methylene chloride, under stirring, and after it has all been added, stirring is continued at -70° C. for 15 hours. After heating to ambient temperature, aqueous soda solution is added, under vigorous stirring, and the organic phase is separated from the aqueous phase, washed with water, and dried with sodium sulfate. The residue remaining after the methylene chloride has been distilled off is recrystallized from isopropanol/diisopropyl ether.

Workup

  1. additionall been added
  2. stirringstirring
  3. additionaqueous soda solution is added, under vigorous stirring
  4. customthe organic phase is separated from the aqueous phase
  5. washwashed with water
  6. dry with materialdried with sodium sulfate
  7. distillationhas been distilled off
  8. customis recrystallized from isopropanol/diisopropyl ether

Sources & evidence

ORD record
ord-061dce232155409c900fda7311d65e29
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Reaction notes

Loading…