Acetaldehyde → HCID 86669135, compound

HRID 2366852Notes

Reaction equation

HRID 2366852 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[Br:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.[CH:18](=O)[CH3:19]>C1(C)C=CC=CC=1>[N:1]1([CH:18]([NH:15][C:14]2[CH:16]=[CH:17][C:11]([Br:10])=[CH:12][CH:13]=2)[CH3:19])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 78074-BromoanilineHCID 178418385HCID 178418385, compound

Product 1

HCID 86669135HCID 86669135, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a suspension of benzotriazole (139 g, 1.16 mol) in toluene (2 L) in a 3 L, four neck flask under nitrogen atmosphere was added at room temperature a solution of 4-bromoaniline (200 g, 1.16 mol) in toluene (300 mL). Then, via an addition funnel was added drop wise acetaldehyde (64.7 ml, 1.17 mol) in solution in toluene (200 mL). The reaction mixture becomes progressively homogenous and then gives a precipitate. The resulting mixture is stirred for 12 hours under nitrogen atmosphere and then filtered. The precipitate is recrystallised in toluene to afford the title compound as a white solid (304 g, 82%).

Workup

  1. customgives a precipitate
  2. filtrationfiltered
  3. customThe precipitate is recrystallised in toluene

Sources & evidence

ORD record
ord-e79747ebf7b94c2880fb3b7c34465726
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

Loading…