Hydrogen Peroxide → HCID 20433307, compound

HRID 1154512Notes

Reaction equation

HRID 1154512 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[CH:10]=[C:11]1[C:16](=[O:17])[N:15]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:14]2[CH:23]=[CH:24][CH:25]=[CH:26][C:13]=2[S:12]1.C[Si](C)(C)Cl.[OH:32]O.O>C(Cl)(Cl)Cl>[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[CH:10]1[C:11](=[O:32])[C:16](=[O:17])[N:15]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:14]2[CH:23]=[CH:24][CH:25]=[CH:26][C:13]=2[S:12]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962Water2×HCID 6397ChlorotrimethylsilaneHCID 70447589HCID 70447589, compound

Product 1

HCID 20433307HCID 20433307, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The solution of 2-(2,4-dichlorophenylmethylidene)-4-(2-dimethylaminoethyl)-2H-1,4-benzothiazine-3(4H)-one hydrochloride (1 g) in 10 ml of chloroform was cooled below 0° C. and added with trimethylchlorosilane (2 ml), and then added with 30% hydrogen peroxide (0.29 g) for 30 minutes. The solution was stirred for 30 minutes below 0° C., and added with 1 ml of water. After further stirring for 1 hour at room temperature, 10 ml of water was added to the reaction mixture. The aqueous phase of the mixture was adjusted to a pH within 8-9 and the chloroform layer was separated from the mixture. The remaining aqueous phase was extracted with 10 ml of chloroform. The chloroform solutions wee combined, dried and evaporated under reduced pressure. The oily residue was purified by silicagel chromatography to give 2-(2,4-dichlorophenyl)-5-(2-dimethylaminoethyl)-2,3-dihydro-1,5-benzothiazepine-3,4(5H)-dione (1.0 g) as oil.

Workup

  1. stirringAfter further stirring for 1 hour at room temperature
  2. customthe chloroform layer was separated from the mixture
  3. extractionThe remaining aqueous phase was extracted with 10 ml of chloroform
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe oily residue was purified by silicagel chromatography

Sources & evidence

ORD record
ord-b5d9796eb43b48acadfe16ceec4c2c06
Source dataset
uspto-grants-1984_12
Patent number
US04490292

Reaction notes

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