Water → Sodium 3,5-di-(2,4-di-tert-amylphenoxypropylcarbamoyl)benzenesulfinate

HRID 1031058

Reaction equation

HRID 1031058 reaction equation
S([O-])([O-])=O.[Na+:5].[Na+].C(=O)([O-])O.[Na+].O.[C:13]([CH:18]([CH2:56][O:57][C:58]1[CH:63]=[CH:62][C:61]([C:64]([CH2:67][CH3:68])([CH3:66])[CH3:65])=[CH:60][CH:59]=1)[CH2:19][NH:20][C:21]([C:23]1[CH:24]=[C:25]([S:52](Cl)(=[O:54])=[O:53])[CH:26]=[C:27]([C:29](=[O:51])[NH:30][CH2:31][CH:32]([C:46]([CH2:49][CH3:50])([CH3:48])[CH3:47])[CH2:33][O:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([CH2:44][CH3:45])([CH3:43])[CH3:42])=[CH:37][CH:36]=2)[CH:28]=1)=[O:22])([CH2:16][CH3:17])([CH3:15])[CH3:14]>C(#N)C>[C:13]([CH:18]([CH2:56][O:57][C:58]1[CH:59]=[CH:60][C:61]([C:64]([CH2:67][CH3:68])([CH3:65])[CH3:66])=[CH:62][CH:63]=1)[CH2:19][NH:20][C:21]([C:23]1[CH:24]=[C:25]([S:52]([O-:54])=[O:53])[CH:26]=[C:27]([C:29](=[O:51])[NH:30][CH2:31][CH:32]([C:46]([CH2:49][CH3:50])([CH3:47])[CH3:48])[CH2:33][O:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([CH2:44][CH3:45])([CH3:43])[CH3:42])=[CH:37][CH:36]=2)[CH:28]=1)=[O:22])([CH2:16][CH3:17])([CH3:14])[CH3:15].[Na+:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 867440573,5-Di-(2,4-di-tert-amylphenoxypropylcarbamoyl)benzenesulfonyl chloride

Product 1

HCID 67635903Sodium 3,5-di-(2,4-di-tert-amylphenoxypropylcarbamoyl)benzenesulfinateYield 82.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
30 °C

Procedure

To 2 g (0.016 mol) of sodium sulfite and 2.4 g (0.029 mol) of sodium hydrogen carbonate were added 100 ml of water and 20 ml of acetonitrile and the mixture was stirred at 30° C. To the mixture was added dropwise a solution of 10.5 g (0.013 mol) of 3,5-di-(2,4-di-tert-amylphenoxypropylcarbamoyl)benzenesulfonyl chloride obtained in the aforesaid step dissolved in 100 ml of acetonitrile. After stirring the resultant mixture for one hour, the reaction mixture was poured onto ice water and extracted with 150 ml of ethyl acetate. The ethyl acetate layer was washed thrice with cold water and dried over Glauber's salt. After filtrating away the Glauber's salt, the residue was concentrated to dryness to provide 8.6 g (yield of 82.8%) of a solid product.

Workup

  1. customobtained in the aforesaid step
  2. additionthe reaction mixture was poured onto ice water
  3. extractionextracted with 150 ml of ethyl acetate
  4. washThe ethyl acetate layer was washed thrice with cold water
  5. dry with materialdried over Glauber's salt
  6. filtrationAfter filtrating away the Glauber's salt
  7. concentrationthe residue was concentrated to dryness

Sources & evidence

ORD record
ord-2a42b137c8104b6683811435928488ad
Source dataset
uspto-grants-1992_04
Patent number
US05108876

Linked notes

Loading…