Acetaldehyde → HCID 86669135, compound

HRID 2201320Notes

Reaction equation

HRID 2201320 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 a dropping 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%). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.1 (m, 3H) 4.9 (m, 0.66H) 5.15 (m, 0.33H) 6.5-6.9 (m, 3H) 7.2-8.2 (m, 7H)

Workup

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

Sources & evidence

ORD record
ord-21bd0a6733a24351a62451e70f977f12
Source dataset
uspto-grants-2016_06
Patent number
US09360482B2

Reaction notes

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