4-Hydroxybenzaldehyde → HCID 22285358, compound

HRID 1061638Notes

Reaction equation

HRID 1061638 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)[CH2:11][O:10]1.[OH:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:10])([CH2:12][N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1)[CH2:11][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 222853611-{[2-(2,4-Difluorophenyl)oxiran-2-yl]methyl}-1H-imidazole

Product 1

HCID 22285358HCID 22285358, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 1-[[2-(2,4-difluorophenyl)-oxiranyl]-methyl]-1H-imidazole (P2) (0.5 g, 2.1 mmole), 4-hydroxy-benzaldehyde (0.31 g, 2.5 mmole) K2CO3 (0.41 g, 2.9 mmole), 18-C-6 (25 mg) in 5 ml of DMF is stirred for 6 hours, extracted with dichloromethane, washed with 2N sodium bicarbonate, dried over Na2SO4, filtered and evaporated under reduced pressure in order to obtain 0.957 g of crude product which is purified by chromatography eluting with a CH2Cl2/MeOH mixture 97/3 in order to obtain 0.557 mg of expected product. Rf=0.12 (CH2Cl2/MeOH 97/3).

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with 2N sodium bicarbonate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure in order
  6. customto obtain 0.957 g of crude product which
  7. customis purified by chromatography
  8. washeluting with a CH2Cl2/MeOH mixture 97/3 in order

Sources & evidence

ORD record
ord-b222e74d317a42d7970b9028fcb7da30
Source dataset
uspto-grants-2005_11
Patent number
US06960600B2

Reaction notes

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