Imidazole → 6-Benzyloxy-3-(1-imidazolyl)methyl-4-chromanone

HRID 610376Notes

Reaction equation

HRID 610376 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][CH2:14][C:13](=[CH2:19])[C:12]2=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][CH2:14][CH:13]([CH2:19][N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)[C:12]2=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 144227906-Benzyloxy-3-methylene-4-chromanone

Product 1

HCID 196006266-Benzyloxy-3-(1-imidazolyl)methyl-4-chromanoneYield 64.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.7 g of 6-benzyloxy-3-methylene-4-chromanone and 3.7 g of imidazole in 50 cc of DMF was heated at 60° C. for 1.5 hours. The reaction was allowed to cool, then poured into water and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and evaporated to give 4 g of crude product which was purified by recrystallization from CH2Cl2 /ether to give 3 g of title product, m.p. 108-110° C. MS calculated for C20H18N2O3 : 334.1317; found: 334.1317.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customevaporated
  5. customto give 4 g of crude product which
  6. customwas purified by recrystallization from CH2Cl2 /ether

Sources & evidence

ORD record
ord-271091ac41304fef9d92c3b1c1ba5872
Source dataset
uspto-grants-1999_12
Patent number
US05998451

Reaction notes

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