Diethyl Ether → HCID 178488981, compound

HRID 1194428Notes

Reaction equation

HRID 1194428 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[Br-:12].[NH2:13][N+:14]1[CH:18]=[CH:17][N:16]([CH2:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:15]=1[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1.CCOCC>C(O)(=O)C>[Br-:12].[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[N:13][N+:14]2[CH:18]=[CH:17][N:16]([CH2:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:15]=2[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 74794-(Dimethylamino)BenzaldehydeHCID 178488977HCID 178488977, compound

Product 1

HCID 178488981HCID 178488981, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.50 g of p-(dimethylamino)benzaldehyde are added to a solution of 3.7 g of 1-amino-2-(p-methoxyphenyl)-3-(pivaloylmethyl)imidazolium bromide in 25 ml of glacial acetic acid. The mixture is stirred at room temperature for 15 hours. Then, 20 ml of ether are added thereto and, after an additional 3 hours, the product is removed by filtration. After recrystallization from ethanol/ether, there is obtained 1-[[p-(dimethylamino)benzylidene]amino]-2-(p-methoxyphenyl)-3-(pivaloylmethyl)imidazolium bromide of melting point 241°.

Workup

  1. waitafter an additional 3 hours
  2. customthe product is removed by filtration
  3. customAfter recrystallization from ethanol/ether

Sources & evidence

ORD record
ord-2f0a8971eff048f29c6b5d5af112642f
Source dataset
uspto-grants-1989_03
Patent number
US04814332

Reaction notes

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