Methane, dichloromethoxy- → HCID 178418754, compound

HRID 10729

Reaction equation

HRID 10729 reaction equation
[CH:1]1([C:4]2[NH:5][CH:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=3[O:17][CH3:18])[N:8]=2)[CH2:3][CH2:2]1.[CH3:19][O:20]C(Cl)Cl>[Ti](Cl)(Cl)(Cl)Cl>[CH:1]1([C:4]2[NH:5][CH:6]=[C:7]([C:9]3[C:10]([O:17][CH3:18])=[CH:11][C:12]([O:15][CH3:16])=[C:13]([CH:14]=3)[CH:19]=[O:20])[N:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 178418803HCID 178418803, compound

Product 1

HCID 178418754HCID 178418754, compound

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

Ex-105B: To a solution of 2-cyclopropyl-4-(2,4-dimethoxy-phenyl)-1H-imidazole (0.51 g, 2.09 mmol) was added dichloromethyl methyl ether (0.28 mL, 3.13 mmol) followed by addition of titanium tetrachloride (1.0M in dichloromethane, 8.4 mL, 8.4 mmol) dropwise at 0° C. The solution was allowed to warm up to ambient temperature and stir for 4.5 hours. The reaction mixture was then poured into ice. The aqueous layer was adjusted to pH 12 and extracted with dichloromethane. The combined solution of dichloromethane was washed with saturated solution of sodium bicarbonate, brine, dried over sodium sulfate and concentrated to afford 5-(2-cyclopropyl-1H-imidazol-4-yl)-2,4-dimethoxy-benzaldehyde which was used without further purification. 1H NMR (DMSO-d6) δ 13.95 (bs, 1H), 10.22 (s, 1H), 8.09 (s, 1H), 7.70 (s, 1H), 6.88 (s, 1H), 4.04 (s, 3H), 4.00 (s, 3H), 2.25 (m, 1H), 1.20 (m, 4H). MS m/z=245 ([M+H]+, 100%).

Workup

  1. additionThe reaction mixture was then poured into ice
  2. extractionextracted with dichloromethane
  3. washThe combined solution of dichloromethane was washed with saturated solution of sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fcfe69e46057466bbea048d283df22b7
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Linked notes

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