4-(Dimethylamino)Benzaldehyde → HCID 178437697, compound

HRID 1762370Notes

Reaction equation

HRID 1762370 reaction equation
[Br-:1].[NH2:2][N+:3]1[CH:7]=[CH:6][N:5]([CH2:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[C:4]=1[CH2:15][CH3:16].[CH3:17][N:18]([CH3:27])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1>C(O)(=O)C>[Br-:1].[CH3:17][N:18]([CH3:27])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[N:2][N+:3]2[CH:7]=[CH:6][N:5]([CH2:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:12])[CH3:13])[C:4]=2[CH2:15][CH3:16])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 178437694HCID 178437694, compound

Product 1

HCID 178437697HCID 178437697, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.38 g (8.2 mmol) of 1-amino-2-ethyl-3-(3,3-dimethyl-2-oxobutyl)imidazolium bromide are dissolved in 30 ml of glacial acetic acid, whereupon the solution is treated with 1.22 g (8.2 mmol) of p-dimethylaminobenzaldehyde. After stirring at room temperature 48 hours the product is recrystallized by the addition of ether, chromatographed on 20 g of silica gel (particle size 0.063-0.200 mm) while eluting with methylene chloride/methanol (19:1 v/v) and recrystallized from ethanol/ether. There is obtained 1-[[4-(dimethylamino)benzylidene]amino]-2-ethyl-3-(pivaloylmethyl)imidazolium bromide of melting point 188°-189°.

Workup

  1. customis recrystallized by the addition of ether
  2. customchromatographed on 20 g of silica gel (particle size 0.063-0.200 mm)
  3. washwhile eluting with methylene chloride/methanol (19:1 v/v)
  4. customrecrystallized from ethanol/ether

Sources & evidence

ORD record
ord-a4671caf0b7b4c9dbc2d382c4c95ca84
Source dataset
uspto-grants-1989_05
Patent number
US04831151

Reaction notes

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