Benzyl Bromide → HCID 14499222, compound

HRID 1194510Notes

Reaction equation

HRID 1194510 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[CH:9]=[CH:8]2.[H][H].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O.CN(C=O)C>[CH2:25]([O:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:10]2[CH:9]=[CH:8][C:7]3[C:12](=[CH:13][CH:14]=[C:5]([O:4][CH3:3])[CH:6]=3)[CH:11]=2)=[CH:17][CH:18]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 14499207HCID 14499207, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14499222HCID 14499222, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The oil was removed from 100 mg (50% in oil, 2.1 mmol, Alfa) of sodium hydride dispersion by washing with three portions of petroleum ether then the residue was covered with 10 ml of dry THF. A total of 530 mg (2.00 mmol) of 4-[(6-methoxy-2-naphthyl)amino]phenol (prepared as described in Example 2) was added to the resulting mixture in several portions. The deep purple reaction mixture was stirred for an additional 10 minutes until hydrogen evolution ceased then 1 ml of sieve-dried DMF was added, followed by 240 ul (2.02 mmol, Aldrich) of benzyl bromide. The solution was heated to 50° for 1 hour, cooled, added to 50 ml of H2O and extracted with 50 ml of ethyl acetate. The organic extract was washed with two additional portions of H2O, dried (MgSO4) and concentrated in vacuo to give 690 mg (97%) of crude title compound as a lavender solid, m.p. 155°-157°.

Workup

  1. washby washing with three portions of petroleum ether
  2. temperatureThe solution was heated to 50° for 1 hour
  3. temperaturecooled
  4. extractionextracted with 50 ml of ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with two additional portions of H2O
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fc6930f53244c4380af7110c4b46d4f
Source dataset
uspto-grants-1989_03
Patent number
US04814454

Reaction notes

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