Ammonium Chloride → 1-[5-Amino-3-chloro-2-(5-methyl-benzothiazol-2-ylsulfanyl)-phenyl]-ethanone

HRID 1835547Notes

Reaction equation

HRID 1835547 reaction equation
[Cl:1][C:2]1[C:3]([S:14][C:15]2[S:16][C:17]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:18]=3[N:19]=2)=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.[Cl-].[NH4+]>[Fe].CCO.C1COCC1.O>[NH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([S:14][C:15]2[S:16][C:17]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:18]=3[N:19]=2)=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 221487501-[3-Chloro-2-(5-methyl-benzothiazol-2-ylsulfanyl)-5-nitro-phenyl]-ethanone

Product 1

HCID 221488961-[5-Amino-3-chloro-2-(5-methyl-benzothiazol-2-ylsulfanyl)-phenyl]-ethanoneYield 68%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a solution of 1-[3-chloro-5-nitro-2-(5-methyl-benzothiazol-2-ylsulfanyl)-phenyl]-ethanone (264) (3.87 g, 10.2 mmol) in 2:2:1 of EtOH/THF/H2O, was added ammonium chloride (Aldrich 2.74 g, 51.2 mmol) and iron powder (Aldrich, 2.87 g, 51.2 mmol). The mixture was refluxed for 3 hours. The mixture was filtered through Celite pad while it was hot, washed the Celite pad with EtOAc. The filtrate was diluted with saturated aqueous NaHCO3 solution and was extracted 3× with EtOAc (150 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 (0-15% EtOAc in CH2Cl2) to yield 2.42 g (68%) of compound 276 as a pale yellow solid.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. filtrationThe mixture was filtered through Celite pad while it
  3. washwashed the Celite pad with EtOAc
  4. additionThe filtrate was diluted with saturated aqueous NaHCO3 solution
  5. extractionwas extracted 3× with EtOAc (150 mL)
  6. washwashed twice with a brine solution (100 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under vacuum
  9. customThe crude solid was chromatographed (0-15% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-4c71710c170542ea8f7cdeabb5098409
Source dataset
uspto-grants-2004_08
Patent number
US06770648B2

Reaction notes

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