Water → 3-Chloro-4-(1,1-dioxo-[1,2]thiazinan-2-yl)-toluene

HRID 1629868Notes

Reaction equation

HRID 1629868 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:3]=1[NH:4][S:5]([CH2:8][CH2:9][CH2:10][CH2:11]Cl)(=[O:7])=[O:6].[K].CC(C)([O-])C.O>CN(C=O)C>[Cl:1][C:2]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:3]=1[N:4]1[CH2:11][CH2:10][CH2:9][CH2:8][S:5]1(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 50987170Potassium tertbutoxideHCID 670486822-chloro-N-(4-chlorobutyl-sulphonyl)-4-methyl-aniline

Product 1

HCID 667317213-Chloro-4-(1,1-dioxo-[1,2]thiazinan-2-yl)-toluene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.27 g (4.29 mmol) 2-chloro-N-(4-chlorbutyl-sulphonyl)-4-methyl-aniline are stirred together with 722 mg (6.43 mmol) potassium-tert.-butoxide in 50 ml DMF for 16 hours at 60° C. Then the reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated down i. vac. The residue is purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate=3:2).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. customevaporated down i
  4. customThe residue is purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate=3:2)

Sources & evidence

ORD record
ord-604a57367f85406f83fb10c8d093e5d6
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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