Water → 4-(2-Amino-4-benzylamino-phenylsulfanyl)-phenol

HRID 607205Notes

Reaction equation

HRID 607205 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[C:11]([N+:23]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].O1CCCC1.O>CO.[Fe]>[NH2:23][C:11]1[CH:10]=[C:9]([NH:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 668084764-(4-Benzylamino-2-nitro-phenylsulfanyl)-phenol

Product 1

HCID 668084094-(2-Amino-4-benzylamino-phenylsulfanyl)-phenolYield 66.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent2×

Procedure

A solution of the product of Example 84B (0.5 g, 1.4 mmol), iron powder (0.49 g, 8.74 mmol) and ammonium chloride (0.50 g, 9.3 mmol) in a methanol (10 mL), tetrahydrofuran (10 mL), and water (5 mL) solution was heated to reflux for 1.5 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 washed with 10% sodium chloride then dried over magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (0.30 g, 66%).

Workup

  1. temperatureto reflux for 1.5 hours
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate was concentrated under vacuum to a volume of 10 mL
  4. additionthe solution diluted with water (50 mL)
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. washThe combined extracts were washed with 10% sodium chloride
  7. dry with materialthen dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ad37f6ac19284108b6523d7df61c7c3e
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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