Acetic Acid → 4-(4-Benzylamino-2-nitro-phenylsulfanyl)-phenol

HRID 607204Notes

Reaction equation

HRID 607204 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:19]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 668084374-(4-Amino-2-nitro-phenylsulfanyl)-phenol

Product 1

HCID 668084764-(4-Benzylamino-2-nitro-phenylsulfanyl)-phenolYield 77.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product of Example 84A (0.63 g, 2.4 mmol), benzaldehyde (0.24 g, 2.3 mmol) and sodium cyanoborohydride (0.15 g, 2.4 mmol) in methanol (10 mL) containing 1% acetic acid was stirred at room temperature for 16 hours. The reaction mixture was quenched with water (20 mL) and the resultant solution was concentrated under vacuum to a yellow solid. The solid was dissolved in ethyl acetate (50 mL), and washed with water, 10% sodium bicarbonate and 10% sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered and solvent removed under vacuum leaving a light yellow oil. The oil was purified by silica gel chromatography eluting with 1% methanol in methylene chloride to provide the title compound (0.63 g, 77%).

Workup

  1. customThe reaction mixture was quenched with water (20 mL)
  2. concentrationthe resultant solution was concentrated under vacuum to a yellow solid
  3. dissolutionThe solid was dissolved in ethyl acetate (50 mL)
  4. washwashed with water, 10% sodium bicarbonate and 10% sodium chloride
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customsolvent removed under vacuum
  8. customleaving a light yellow oil
  9. customThe oil was purified by silica gel chromatography
  10. washeluting with 1% methanol in methylene chloride

Sources & evidence

ORD record
ord-f4224b0780894c1eb1bd1972861539a8
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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