Triphenylphosphine → 4-(Aminomethyl)-5-bromo-2-ethoxy-N-methylbenzamide

HRID 1296030Notes

Reaction equation

HRID 1296030 reaction equation
[CH3:1][NH:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([CH2:11][N:12]=[N+]=[N-])=[CH:6][C:5]=1[O:15][CH2:16][CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[CH3:1][NH:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([CH2:11][NH2:12])=[CH:6][C:5]=1[O:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 22929709HCID 22929709, compound

Product 1

HCID 229297314-(Aminomethyl)-5-bromo-2-ethoxy-N-methylbenzamideYield 104.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

After dissolving the N1-methyl-4-(azidomethyl)-5-bromo-2-ethoxybenzamide (5.32 g) in tetrahydrofuran (50 ml) and water (3 ml), triphenylphosphine (5.4 g) was added and the mixture was stirred at room temperature for 4 days. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (5.11 g) as a light yellow solid.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4fc77f5f4b9f41d2bcc28223c4f7a922
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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