Pyridine → HCID 54426938, compound

HRID 487699Notes

Reaction equation

HRID 487699 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[S:12][C:13]4[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]=4[N:20]=3)=[CH:8][C:7]=2[CH:21]=1.N1C=CC=CC=1.[C:28](Cl)(=[O:30])[CH3:29]>CN(C)C=O.ClCCl.[Cl-].[Na+].O>[C:28]([CH:18]1[CH2:17][CH2:16][CH2:15][NH:14][C:13]2[S:12][C:11]([C:9]3[O:10][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:21][C:7]=4[CH:8]=3)=[N:20][C:19]1=2)(=[O:30])[CH3:29]

Participants

7

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 19092742HCID 19092742, compound

Product 1

HCID 54426938HCID 54426938, compoundYield 72.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a cooled solution of 2-(5-methoxybenzofuran-2-yl)-4,5,6,7-tetrahydro-8H-thiazolo[5,4-b]azepine (1.3 g) and pyridine (0.65 ml) in N,N-dimethylformamide (20 ml), a solution of acetyl chloride (0.41 g) in dichloromethane (2 ml) was added dropwise below 10° C. After being stirred for 2 hours, the resulting mixture was poured into brine and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup, which was crystallized from ethanol and collected by filtration to give 8-acetyl-2-(5-methoxybenzofuran-2-yl) 4,5,6,7-tetrahydro-8H-thiazolo[5,4-b]azepine (1.07 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a syrup, which
  6. customwas crystallized from ethanol
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ed436730221446aabca46381a1e0d334
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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