Ammonium Chloride → HCID 178486612, compound

HRID 480474Notes

Reaction equation

HRID 480474 reaction equation
C(OC[N:10]1[CH:14]=[C:13](I)[N:12]=[CH:11]1)C1C=CC=CC=1.C([Mg]Br)C.[CH3:20][O:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][C:31]=1[O:32][CH3:33])[CH:28]=[C:27]([C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])[CH:26]=[CH:25]2.[Cl-].[NH4+]>ClCCl.C1COCC1.O>[CH3:20][O:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][C:31]=1[O:32][CH3:33])[CH:28]=[C:27]([C@@:34]([C:14]1[N:10]=[CH:11][NH:12][CH:13]=1)([OH:38])[CH:35]([CH3:36])[CH3:37])[CH:26]=[CH:25]2

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 10860166HCID 10860166, compoundHCID 114142376,7-dimethoxy-2-isobutyrylnaphthaleneHCID 178418443HCID 178418443, compound

Product 1

HCID 178486612HCID 178486612, compoundYield 71.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

1-benzyloxymethyl-4-iodoimidazole (31.5 g) was dissolved in dichloromethane (500 mL) under argon atmosphere. A solution of ethylmagnesium bromide in THF (0.96M; 110 mL) was added dropwise to the solution with keeping the reaction temperature below 8° C. and the mixture was stirred for 1 h. A solution of 6,7-dimethoxy-2-isobutyrylnaphthalene (31 g) in dichloromethane (50 mL) was added to the mixture and stirred at room temperature for 24 h. Saturated ammonium chloride solution (150 mL) and water (350 mL) were added to the mixture, and organic layer was concentrated. The residue was dissolved in THF (200 mL)-ethyl acetate (1 L), washed with water and brine, dried over Na2SO4 and concentrated in vacuo to one tenth of initial volume. The crystals were collected and washed with ethyl acetate to give the titled compound (23.4 g) as colorless crystals. Second crystals (4.53 g) were recovered from the mother liquor.

Workup

  1. customthe reaction temperature below 8° C.
  2. stirringstirred at room temperature for 24 h
  3. concentrationwas concentrated
  4. dissolutionThe residue was dissolved in THF (200 mL)-ethyl acetate (1 L)
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo to one tenth of initial volume
  8. customThe crystals were collected
  9. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-5faf2e51b10b4a04bfabc8f63869956d
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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