Ammonium Chloride → 4-[2-Amino-4-(1-phenyl-ethoxy)-phenylsulfanyl]-phenol

HRID 607177Notes

Reaction equation

HRID 607177 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17][C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[C:13]([N+:25]([O-])=O)[CH:12]=2)[CH3:9])=[CH:4][CH:3]=1.[NH4+].[Cl-]>CO.[Fe]>[NH2:25][C:13]1[CH:12]=[C:11]([O:10][CH:8]([C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)[CH3:9])[CH:16]=[CH:15][C:14]=1[S:17][C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 668082204-{4-[1-(4-Bromo-phenyl)-ethoxy]-2-nitro-phenylsulfanyl}-phenol

Product 1

HCID 668084394-[2-Amino-4-(1-phenyl-ethoxy)-phenylsulfanyl]-phenolYield 104.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

The product from Example 22C (560 mg, 1.25 mmol) was reacted with Fe (279 mg, 5.0 mmol) and NH4Cl (76 mg, 1.40 mmol) in 5 mL MeOH/5 mL THF/2.5 mL water following the procedure from Example 10E giving the title compound as a solid (439 mg, 84%).

Sources & evidence

ORD record
ord-dd263af3d65e4d8985e2694af832d05a
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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