Dimethylformamide diethylacetal → HCID 86742772, compound

HRID 1383116Notes

Reaction equation

HRID 1383116 reaction equation
[Cl-:1].[CH3:2][N:3]([CH3:29])[C:4]1[CH:28]=[CH:27][C:7]([CH:8]=[N:9][N+:10]2[CH:14]=[CH:13][N:12]([N:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[C:11]=2[CH3:26])=[CH:6][CH:5]=1.C(O[CH:33](OCC)[N:34]([CH3:36])[CH3:35])C>C(O)CC>[Cl-:1].[CH3:25][N:23]([CH3:24])[C:20]1[CH:21]=[CH:22][C:17]([CH:16]=[N:15][N+:12]2[CH:13]=[CH:14][N:10]([N:9]=[CH:8][C:7]3[CH:6]=[CH:5][C:4]([N:3]([CH3:2])[CH3:29])=[CH:28][CH:27]=3)[C:11]=2[CH:26]=[CH:33][N:34]([CH3:36])[CH3:35])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 70351311HCID 70351311, compound

Product 1

HCID 86742772HCID 86742772, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

2.05 g of 1,3-bis[[p-(dimethylamino)benzylidene]amino]-2methylimidazolium chloride and 7.35 g of N,N-dimethylformamide diethyl acetal are stirred at 100° for 45 minutes in 150 ml of 1-propanol. The product is precipitated by the addition of ether. It is crystallized from dichloromethane/methanol and recrystallized from ethanol. There is obtained 1,3-bis[[p-(dimethylamino)benzylidene]amino]-2-[2-(dimethylamino)vinyl]imidazolium chloride of melting point 246°-248°.

Workup

  1. customThe product is precipitated by the addition of ether
  2. customIt is crystallized from dichloromethane/methanol
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a7e60b35f8614653adccf839b3a26c32
Source dataset
uspto-grants-1989_02
Patent number
US04808727

Reaction notes

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