Diethyl Ether → HCID 178437686, compound

HRID 1762381Notes

Reaction equation

HRID 1762381 reaction equation
[Br-:1].[NH2:2][N+:3]1[CH:7]=[CH:6][N:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[O:10])[C:4]=1[CH2:18][CH3:19].[CH3:20][N:21]([CH3:30])[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.CCOCC>C(O)(=O)C>[Br-:1].[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:9](=[O:10])[CH2:8][N:5]2[CH:6]=[CH:7][N+:3]([N:2]=[CH:26][C:25]3[CH:28]=[CH:29][C:22]([N:21]([CH3:30])[CH3:20])=[CH:23][CH:24]=3)=[C:4]2[CH2:18][CH3:19])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 74794-(Dimethylamino)BenzaldehydeHCID 178437682HCID 178437682, compound

Product 1

HCID 178437686HCID 178437686, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension consisting of 1.72 g (5 mmol) of 1-amino-3-(p-chlorophenacyl)-2-ethylimidazolium bromide and 0.74 g (5 mmol) of 4-dimethylaminobenzaldehyde in 15 ml of glacial acetic acid is stirred at room temperature for 48 hours, treated with ether and filtered. The filtered-off crude product is chromatographed on 30 g of silica gel (particle size 0.063-0.200 mm) while eluting with methylene chloride/methanol (9:1 v/v) and then recrystallized from methylene chloride/methanol/ether. There is obtained 3-(p-chlorophenacyl)-1-[[p-(dimethylamino)benzylidene]amino]-2-ethylimidazolium bromide of melting point 252°-253°.

Workup

  1. filtrationfiltered
  2. customThe filtered-off crude product is chromatographed on 30 g of silica gel (particle size 0.063-0.200 mm)
  3. washwhile eluting with methylene chloride/methanol (9:1 v/v)
  4. customrecrystallized from methylene chloride/methanol/ether

Sources & evidence

ORD record
ord-bfa088fb141346d68d4140c3662deec2
Source dataset
uspto-grants-1989_05
Patent number
US04831151

Reaction notes

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