Water → HCID 22990069, compound

HRID 1169439Notes

Reaction equation

HRID 1169439 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[CH2:16][CH2:17][O:18][C:19]3[CH:25]=[CH:24][C:23](C4C=CC=CC=4C)=[CH:22][C:20]=3[CH:21]=2)=[O:14])=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:40](Cl)(=[O:42])[CH3:41].O>C1COCC1.CN(C=O)C>[C:40]([N:3]1[CH2:4][CH2:5][N:1]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[CH2:16][CH2:17][O:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[CH:21]=2)=[O:14])=[CH:8][CH:7]=1)(=[O:42])[CH3:41]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22990037HCID 22990037, compound

Product 1

HCID 22990069HCID 22990069, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

Into a solution of N-[4-(imidazolin-2-yl)phenyl]-7-(methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (120 mg) in THF/DMF (10 ml/1 ml) were added triethylamine (0.09 ml) and acetyl chloride (0.024 ml), and the resulting mixture was stirred at room temperature for one hour. The reaction mixture was mixed with water under ice cooling and was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride, was dried (anhydrous magnesium sulfate) and was then concentrated. The residue was subjected to purification using silica gel column chromatography (ethyl acetate/methanol) and further to recrystallization from ethyl acetate/methanol to obtain N-[4-(acetyl-2-imidazolin-2-yl)phenyl]-2,3-dihydro-1-benzooxepine-4-carboxamide (compound 93) (56 mg) as colorless crystals.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialwas dried (anhydrous magnesium sulfate)
  4. concentrationwas then concentrated
  5. customThe residue was subjected to purification
  6. customfurther to recrystallization from ethyl acetate/methanol

Sources & evidence

ORD record
ord-f245ac9213bc4bb1a68322f6a12be5a0
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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