Benzyl Bromide → Phenylmethyl 3-{2-[(2,6-dibromo-4-methylphenyl)methylidene]hydrazino}benzoate

HRID 1925589Notes

Reaction equation

HRID 1925589 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([Br:15])[C:9]=1[CH:16]=[N:17][NH:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([OH:24])=[O:23].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[Br:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([Br:15])[C:9]=1[CH:16]=[N:17][NH:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([O:24][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:23]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 671571683-{2-[(2,6-Dibromo-4-methylphenyl)methylidene]hydrazino}benzoic acid

Product 1

HCID 67157526Phenylmethyl 3-{2-[(2,6-dibromo-4-methylphenyl)methylidene]hydrazino}benzoateYield 103.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (7.41 g, 53.61 mmol) was added to a solution of 3-{2-[(2,6-dibromo-4-methylphenyl)methylidene]hydrazino}benzoic acid (19.4 g, 44.65 mmol) in dry DMF (200 mL). Benzyl bromide (5.42 mL, 45.6 mmol) was then added and the mixture stirred at room temperature for 15 hours and then partitioned between ethyl acetate (500 mL) and water (500 mL). The organic phase was separated, combined with a second ethyl acetate extract (300 mL), washed successively with water (4×500 mL) and brine (300 mL), dried over anhydrous sodium sulphate, evaporated and further dried under vacuum to give the title compound (23.2 g).

Workup

  1. custompartitioned between ethyl acetate (500 mL) and water (500 mL)
  2. customThe organic phase was separated
  3. extractionextract (300 mL)
  4. washwashed successively with water (4×500 mL) and brine (300 mL)
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated
  7. customfurther dried under vacuum

Sources & evidence

ORD record
ord-8425087f42fe490dbddfe339ff8edd64
Source dataset
uspto-grants-2012_05
Patent number
US08178573B2

Reaction notes

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