Water → 4-[2-Amino-4-(4-methoxy-benzyloxy)-phenylsulfanyl]-phenol
Reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)=[C:11]([N+:23]([O-])=O)[CH:10]=2)=[CH:5][CH:4]=1.[Cl-].[NH4+].O1CCCC1.O>CO.[Fe]>[NH2:23][C:11]1[CH:10]=[C:9]([O:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:27][CH:26]=2)[CH:14]=[CH:13][C:12]=1[S:15][C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1Participants
7
Procedure
A solution of the product of Example 10D (1.06 g, 2.76 mmol), iron powder (0.63 g, 11.04 mmol) and ammonium chloride (0.18 g, 3.31 mmol) in a methanol (18 mL), tetrahydrofuran (18 mL), and water (6 mL) solution was heated to reflux for 3 hours. The resultant mixture was diluted with methanol (50 mL) and filtered through a pad of celite. The filtrate was concentrated under vacuum to a volume of 10 mL, the solution diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined extracts were dried over magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (0.99 g, 100%).
Workup
- temperatureto reflux for 3 hours
- filtrationfiltered through a pad of celite
- concentrationThe filtrate was concentrated under vacuum to a volume of 10 mL
- additionthe solution diluted with water (50 mL)
- extractionextracted with ethyl acetate (2×50 mL)
- dry with materialThe combined extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-a051f61db4f94b33ad6772a489901db3
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915411B2
Reaction notes
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