Triethylamine → 1-[(Benzyloxy)methyl]imidazol-2-yl (3,4-dimethoxy-5-nitrophenyl) ketone

HRID 274532Notes

Reaction equation

HRID 274532 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([N+:28]([O-:30])=[O:29])[C:25]=1[O:26][CH3:27])[C:20](Cl)=[O:21].C(N(CC)CC)C>C(#N)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:20]([C:11]2[N:10]([CH2:9][O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:14]=[CH:13][N:12]=2)=[O:21])[CH:23]=[C:24]([N+:28]([O-:30])=[O:29])[C:25]=1[O:26][CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 147959081-BenzyloxymethylimidazoleHCID 219286153,4-Dimethoxy-5-nitrobenzoyl chloride

Product 1

HCID 190001721-[(Benzyloxy)methyl]imidazol-2-yl (3,4-dimethoxy-5-nitrophenyl) ketone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 10.0 g of 1-[(benzyloxy)- methyl]imidazole in 50 ml of acetonitrile is added dropwise within 10 minutes while cooling with ice to a solution of 13.0 g of 3,4-dimethoxy-5-nitrobenzoyl chloride and 5.4 g of triethylamine in 80 ml of acetonitrile so that the temperature does not exceed 25° . The mixture is subsequently stirred for an additional 3 hours, whereupon the solvent is distilled. After treatment with water, the mixture is extracted with ethyl acetate. After two-fold washing with water, the organic phase is dried over sodium sulfate and evaporated. The resulting oil is chromatographed on 600 g of silica gel with toluene/ethyl acetate (95:5). There is obtained 1-[(benzyloxy)methyl]imidazol-2-yl (3,4-dimethoxy-5-nitrophenyl) ketone as a yellowish oil.

Workup

  1. customdoes not exceed 25°
  2. distillationis distilled
  3. extractionAfter treatment with water, the mixture is extracted with ethyl acetate
  4. dry with materialAfter two-fold washing with water, the organic phase is dried over sodium sulfate
  5. customevaporated
  6. customThe resulting oil is chromatographed on 600 g of silica gel with toluene/ethyl acetate (95:5)

Sources & evidence

ORD record
ord-04cc483c3e344de4b3a61033c0a61542
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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