Hydrochloric Acid → HCID 22382443, compound

HRID 895880Notes

Reaction equation

HRID 895880 reaction equation
[C:1]1([C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][O:3]1)=[O:2].Cl.[CH3:12][NH:13][O:14][CH3:15].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl.C(N(CC)CC)C>[OH:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[C:1]([N:13]([O:14][CH3:15])[CH3:12])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6885PhthalideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 6451240Aluminum(III) Chloride

Product 1

HCID 22382443HCID 22382443, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of phthalide (26.8 g) in methylene chloride (600 ml) were successively added N,O-dimethylhydroxylamine hydrochloride (58.5 g) and aluminum chloride (40.0 g) under ice-cooling, and triethylamine (139 ml) was added dropwise over 40 min. The mixture was stirred at room temperature for 12 hr. The reaction mixture was poured into diluted hydrochloric acid, and the organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 2-hydroxymethyl-N-methoxy-N-methylbenzamide. The obtained 2-hydroxymethyl-N-methoxy-N-methylbenzamide was dissolved in N,N-dimethylformamide (300 ml), and imidazole (9.53 g) and tert-butyldimethylchlorosilane (21.1 g) were added. The mixture was stirred at room temperature for 3.5 hr and the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentration under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3) to give the title compound (42.0 g).

Workup

  1. temperaturecooling
  2. washthe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-23917d0faae7499ea03c0885f0906910
Source dataset
uspto-grants-2005_07
Patent number
US06916956B2

Reaction notes

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