Acetic Acid → HCID 11284868, compound

HRID 606275Notes

Reaction equation

HRID 606275 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[Cl:18].[OH-].[Na+].[Cl:26][C:27]1[CH:28]=[C:29]([N:34]=[C:35]=[S:36])[CH:30]=[CH:31][C:32]=1[Cl:33].C(O)(=O)C>CC(C)=O.CCCCCC.O>[Cl:1][C:2]1[CH:3]=[C:4]([S:20]([NH:23][C:35]([NH:34][C:29]2[CH:30]=[CH:31][C:32]([Cl:33])=[C:27]([Cl:26])[CH:28]=2)=[S:36])(=[O:21])=[O:22])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[Cl:18]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 230651,2-Dichloro-4-isothiocyanatobenzeneHCID 2798152HCID 2798152, compound

Product 1

HCID 11284868HCID 11284868, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

40 mg of 3,5-dichloro-4-(2-chloro-4-nitro phenoxy) benzenesulfonamide (0.1 m.mol) was dissolved in 2.5 ml of acetone. 0.5 ml of 1N NaOH was added to this and the mixture shaken for 30 mins at room temperature. 0.1 m.mole of 3,4-Dichlorophenyl isothiocyanate was added and the reaction stirred at 45° C. for 4 hours. The reaction mixture was neutralized by addition of 1N acetic acid. This was followed by addition of 3 ml of water. The white precipitate formed was extracted with ethyl acetate. The ethyl acetate was evaporated and the residue obtained was purified by radial silica-gel chromatography using 1:4 ethyl acetate:hexane as eluant to give 50.5 mg of desired product as a white solid (84% yield).

Workup

  1. stirringthe reaction stirred at 45° C. for 4 hours
  2. customThe white precipitate formed
  3. extractionwas extracted with ethyl acetate
  4. customThe ethyl acetate was evaporated
  5. customthe residue obtained
  6. customwas purified by radial silica-gel chromatography

Sources & evidence

ORD record
ord-b385c5a61b404120a99167b2234ca1e9
Source dataset
uspto-grants-2011_03
Patent number
US07915293B2

Reaction notes

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