Hydrochloric Acid → HCID 67254882, compound

HRID 1835550Notes

Reaction equation

HRID 1835550 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([S:20][C:21]2[S:22][C:23]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][C:24]=3[N:25]=2)=[C:15]([Cl:32])[CH:14]=1)(=[O:11])=[O:10].[OH-:33].[K+].Cl>C(O)(C)(C)C>[Cl:19][C:17]1[CH:18]=[C:13]([NH:12][S:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])(=[O:11])=[O:10])[CH:14]=[C:15]([Cl:32])[C:16]=1[S:20][C:21]1[S:22][C:23]2[CH:29]=[CH:28][C:27]([C:30]([NH2:31])=[O:33])=[CH:26][C:24]=2[N:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22148783HCID 22148783, compound

Product 1

HCID 67254882HCID 67254882, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 2,4-dichloro-N-[3,5-dichloro-4-(5-cyano-benzothiazol-2-ylsulfanyl)-phenyl]-benzenesulfonamide (297) (250 mg, 0.45 mmol) in tert-butanol (10 mL), was added KOH (EM Science Product, 126 mg, 2.25 mmol). The resulting mixture was refluxed for 1 hour. After cooling to room temperature, a 1M aqueous solution of HCl (50 mL) was added and the crude reaction mixture was extracted 3× with EtOAc (50 mL). The organic layers were combined and washed twice with a brine solution (100 mL), dried over Na2SO4, and concentrated under vacuum. The crude solid was chromatographed (20% EtOAc in CH2Cl2, then 10% MeOH in CH2Cl2) to yield 207 mg (80%) of compound 303 as a white solid.

Workup

  1. temperatureThe resulting mixture was refluxed for 1 hour
  2. customthe crude reaction mixture
  3. extractionwas extracted 3× with EtOAc (50 mL)
  4. washwashed twice with a brine solution (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe crude solid was chromatographed (20% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-4b192753ab3545d88a1fd255dccf2a5f
Source dataset
uspto-grants-2004_08
Patent number
US06770648B2

Reaction notes

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