Sodium Hydroxide → HCID 22595761, compound

HRID 2268784Notes

Reaction equation

HRID 2268784 reaction equation
CC(N1CC2C=C(SC)C=CC=2N(CC=C)S1(=O)=[O:19])C.[Cl:21][CH2:22][CH2:23][N:24]1[C:29]2[CH:30]=[CH:31][C:32]([S:34][CH3:35])=[CH:33][C:28]=2[CH2:27][N:26]([CH:36]([CH3:38])[CH3:37])[S:25]1(=[O:40])=[O:39].ClC1C=CC=C(C(OO)=O)C=1.[OH-:52].[Na+]>O.C(Cl)(Cl)Cl>[Cl:21][CH2:22][CH2:23][N:24]1[C:29]2[CH:30]=[CH:31][C:32]([S:34]([CH3:35])(=[O:19])=[O:52])=[CH:33][C:28]=2[CH2:27][N:26]([CH:36]([CH3:38])[CH3:37])[S:25]1(=[O:40])=[O:39]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 22595722HCID 22595722, compoundHCID 22595755HCID 22595755, compound

Product 1

HCID 22595761HCID 22595761, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A 500 mL 3 necked flask equipped thermometer, pressure equalized dropping funnel, nitrogen bubbler and magnetic stirrer bar was charged with 1-(2-chloroethyl)-3,4-dihydro-3-(1-methylethyl)-6-methylthio-1H-2,1,3-benzothiadiazine-2,2-dioxide (10.0 g, 0.0299 mol) and chloroform (200 ml). To this solution was added in one portion m-chloroperbenzoic acid (20.6 g , ˜4 equivalents, nominal purity 56-86%), this resulted in an exotherm which raised the temperature from 20° C. to 50° C. This solution was then stirred for 15 mins, water (100 ml) was added then 2M sodium hydroxide (100 ml). The organic layer was separated, washed again with 2M sodium hydroxide (100 ml), then water (100 ml) dried (MgSO4), filtered and the filtrate evaporated under reduced pressure to leave a white-cream foam, which was dried at 45° C. in vacuo to yield the product.

Workup

  1. customthis resulted in an exotherm which
  2. temperatureraised the temperature from 20° C. to 50° C
  3. customThe organic layer was separated
  4. washwashed again with 2M sodium hydroxide (100 ml)
  5. dry with materialwater (100 ml) dried (MgSO4)
  6. filtrationfiltered
  7. customthe filtrate evaporated under reduced pressure
  8. customto leave a white-cream foam, which
  9. customwas dried at 45° C. in vacuo
  10. customto yield the product

Sources & evidence

ORD record
ord-2980f0c758874e41977b16a30bd126c2
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

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