Sodium Sulfite → 5-(2,6-Dichloro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one

HRID 2191510Notes

Reaction equation

HRID 2191510 reaction equation
O.O.O.O.O.O.O.O.O.O.O.O.P([O-])([O-])(O)=O.[Na+].[Na+].S([O-])([O-])=O.[Na+].[Na+].[O:26]=[C:27]1[CH2:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32]([S:36](Cl)(=[O:38])=[O:37])[CH:33]=2)[NH:28]1.[Cl:40][C:41]1[CH:48]=[CH:47][CH:46]=[C:45]([Cl:49])[C:42]=1[CH2:43]Br>O.CC(C)=O>[Cl:40][C:41]1[CH:48]=[CH:47][CH:46]=[C:45]([Cl:49])[C:42]=1[CH2:43][S:36]([C:32]1[CH:33]=[C:34]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27](=[O:26])[CH2:35]2)(=[O:38])=[O:37]

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 61456Phosphoric acid, disodium salt, dodecahydrateHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 181797685-(2,6-Dichloro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-oneYield 88.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

Sodium monohydrogen phosphate dodecahydrate (142 g, 1.0 mol) and sodium sulfite (252 g, 2.0 mol) were dissolved in 2 L of water at room temperature, heated to 30° C., and added with 2-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride 64b (232 g, 1.0 mol). Upon completion of the addition, the reaction mixture was stirred at 60° C. for 16 hours. A solution of 2,6-dichlorobenzyl bromide (240 g, 1.0 mol) in acetone (1.8 L) was added to the above solution, stirred at 60° C. for 1 hour, added with another acetone (200 ml) and stirred for another 2 hours. The reaction mixture was quenched with water (5 L), stirred at room temperature for 1 hour and filtered. The filter cake was washed with water (1 L) and acetone (1 L), and dried in vacuo to obtain the title compound 5-(2,6-dichloro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one 64c (314 g, yield 88%) as a white solid.

Workup

  1. additionUpon completion of the addition
  2. stirringstirred at 60° C. for 1 hour
  3. stirringstirred for another 2 hours
  4. customThe reaction mixture was quenched with water (5 L)
  5. stirringstirred at room temperature for 1 hour
  6. filtrationfiltered
  7. washThe filter cake was washed with water (1 L) and acetone (1 L)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-493a1a9f1d364c78bcd4025d3a2222be
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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