Sodium Pyrosulfite → HCID 117600739, compound

HRID 1497723Notes

Reaction equation

HRID 1497723 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:9]([NH:16][CH2:17]C2C=CC(OC)=CC=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]=1.S(S([O-])=O)([O-])(=O)=[O:27].[Na+].[Na+]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][C:17](=[O:27])[NH:16][CH:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 656671Sodium PyrosulfiteHCID 117600113HCID 117600113, compound

Product 1

HCID 117600739HCID 117600739, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Bromo-2-[(4-methoxy-benzylamino)-phenyl-methyl]-phenol (0.30 g, 0.693 mmol) is slurried in acetonitrile (3 mL). An aqueous solution of ceric ammonium nitrate (1.15 g, 2.10 mmol) is slowly added dropwise at room temperature. The reaction mixture is shaken at room temperature for 2 hours. The mixture is poured into an aqueous solution of sodium pyrosulfite and left for half an hour. The aqueous phase is exhaustively extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate. After evaporated to in vacuo the residue is triturated with acetonitrile. The insoluble product is collected by filtration and dried. This provides the desired product.

Workup

  1. waitleft for half an hour
  2. extractionThe aqueous phase is exhaustively extracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customAfter evaporated to in vacuo the residue
  5. customis triturated with acetonitrile
  6. filtrationThe insoluble product is collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-f799573e7cc945d5bb5c0e11f327a6ec
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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