Acetaldehyde → HCID 86669135, compound

HRID 2041686Notes

Reaction equation

HRID 2041686 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 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-6f79c6b920dd417f90e70c1e5b25f26f
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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