1,3-Dichloropropane → 2-(3-Chloropropyl)-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide Ethylene Ketal

HRID 363302

Reaction equation

HRID 363302 reaction equation
[H-].[Na+].[CH2:3]1[O:18][C:6]2([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9](=[O:17])(=[O:16])[NH:8][CH2:7]2)[O:5][CH2:4]1.[Cl:19][CH2:20][CH2:21][CH2:22]Cl>CN(C=O)C>[CH2:3]1[O:18][C:6]2([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9](=[O:17])(=[O:16])[N:8]([CH2:22][CH2:21][CH2:20][Cl:19])[CH2:7]2)[O:5][CH2:4]1

Participants

5

Reactant 3

HCID 88811,3-DichloropropaneHCID 24758Sodium hydrideHCID 218178932H-1,2-benzothiazin-4(3H)-one 1,1-dioxide ethylene ketal

Product 1

HCID 121117312-(3-Chloropropyl)-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide Ethylene KetalYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 2.20 g (50 mmol) of 60% sodium hydride in 100 ml of DMF, a solution of 12.06 g (50 mmol) of 3,4-dihydro-2H-1,2-benzothiazin-4-one 1,1-dioxide ethylene acetal in 50 ml of DMF was added under ice cooling and stirring. The reaction mixture was stirred for 30 minutes at 0° C. and then for further one hour at room temperature. Under ice cooling, a solution of 16.95 g (150 mmol) of 1,3-dichloropropane in 50 ml of DMF was added to the reaction mixture, followed by stirring for 17 hours at room temperature. The post-treatment and purification were conducted as in Example 10, whereby 13.41 g of the title compound were obtained (yield: 84%).

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes at 0° C.
  2. stirringby stirring for 17 hours at room temperature
  3. customThe post-treatment and purification

Sources & evidence

ORD record
ord-20b95a6ce7b8435285369d52bab50899
Source dataset
uspto-grants-1999_02
Patent number
US05874429

Linked notes

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