Ammonium Chloride → N-[4-Amino-5-(4-hydroxy-phenylsulfanyl)-2-methyl-phenyl]-2-phenyl-acetamide

HRID 605290Notes

Reaction equation

HRID 605290 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:10]([N+:26]([O-])=O)=[CH:11][C:12]([CH3:25])=[C:13]([NH:15][C:16](=[O:24])[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+]>O1CCCC1.CO.O.[Fe]>[NH2:26][C:10]1[C:9]([S:8][C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:14][C:13]([NH:15][C:16](=[O:24])[CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:12]([CH3:25])[CH:11]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 67041085N-[5-(4-Hydroxy-phenylsulfanyl)-2-methyl-4-nitro-phenyl]-2-phenyl-acetamide

Product 1

HCID 67040658N-[4-Amino-5-(4-hydroxy-phenylsulfanyl)-2-methyl-phenyl]-2-phenyl-acetamideYield 94.4%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 265B (0.282 g, 0.715 mmol), iron powder (0.160 g, 2.86 mmol, 4.0 eq), and ammonium chloride (0.0469 g, 0.858 mmol, 1.2 eq) in tetrahydrofuran (6 mL), methanol (6 mL) and water (2 mL) was heated under reflux for 1.5 h and then cooled to room temperature. The reaction mixture was then filtered through Celite and the Celite pad rinsed with methanol (50 mL). The filtrate was evaporated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and evaporated to provide an orange oil that was triturated with dichloromethane to provide the title compound as a yellow powder (0.246 g, 94%).

Workup

  1. temperatureunder reflux for 1.5 h
  2. filtrationThe reaction mixture was then filtered through Celite
  3. washthe Celite pad rinsed with methanol (50 mL)
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe residue partitioned between ethyl acetate and water
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto provide an orange oil that
  10. customwas triturated with dichloromethane

Sources & evidence

ORD record
ord-5ddf1344285c4c008c2004f3bb6a0324
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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