Ammonium Chloride → 4-(2-Amino-5-benzyloxy-phenylsulfanyl)-phenol

HRID 607317Notes

Reaction equation

HRID 607317 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:23]([O-])=O)=[C:13]([S:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>O1CCCC1.CO.O.[Fe]>[NH2:23][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][C:13]=1[S:15][C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 668083594-(5-Benzyloxy-2-nitro-phenylsulfanyl)-phenol

Product 1

HCID 668086274-(2-Amino-5-benzyloxy-phenylsulfanyl)-phenolYield 95.6%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 237B (0.390 g, 1.10 mmol), iron powder (0.248 g, 4.41 mmol, 4.0 eq) and ammonium chloride (0.071 g, 1.32 mmol, 1.2 eq) in tetrahydrofuran (6 mL), methanol (6 mL) and water (2 mL) was heated under reflux for 16 hours and then cooled to room temperature. The reaction mixture was filtered through Celite, rinsing with methanol, and the filtrate was evaporated under reduced pressure to provide the title compound (0.340 g, 95%) as a gray powder that was used in subsequent reactions without further purification.

Workup

  1. temperatureunder reflux for 16 hours
  2. filtrationThe reaction mixture was filtered through Celite
  3. washrinsing with methanol
  4. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d6fc048825cc44548167e7565e4707c5
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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