Ammonium Chloride → HCID 66777794, compound

HRID 2091220Notes

Reaction equation

HRID 2091220 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[CH:9][N:8]([CH3:11])[C:7]=2[CH:12]=1.C([Li])CCC.CON(C)[C:21]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH:23]1([C:21]([C:9]2[N:8]([CH3:11])[C:7]3[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[N:10]=2)=[O:22])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 11769007N-methoxy-N-methylcyclohexanecarboxamideHCID 118050756-Methoxy-1-methyl-1H-benzimidazole2×HCID 178418339Butyllithium

Product 1

HCID 66777794HCID 66777794, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution (100 mL) of 6-methoxy-1-methyl-1H-benzoimidazole (4.07 g) synthesized in the above-mentioned (2) in tetrahydrofuran was added a 1.6M solution (30.1 mL) of n-butyllithium in hexane at −78° C., and the mixture was stirred under nitrogen atmosphere for 30 min. A solution (50 mL) of N-methoxy-N-methylcyclohexanecarboxamide (5.15 g) synthesized in the above-mentioned (3) in tetrahydrofuran was added, and the mixture was stirred at −78° C. for 1 hr and at room temperature for 2 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether=1:5, volume ratio) to give the title object compound (5.80 g, 85%) as white crystals.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at −78° C. for 1 hr and at room temperature for 2 hr
  3. customto quench
  4. customthe reaction
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether=1:5, volume ratio)

Sources & evidence

ORD record
ord-8991033417c74fcc957ceb8d77928c4b
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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