Dimethylformamide → HCID 19363314, compound

HRID 850513Notes

Reaction equation

HRID 850513 reaction equation
[NH2:1][C:2]1[C:18]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=[CH:15][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)=[O:5].[C:27](=S)=[S:28].C1CCN2C(=NCCC2)CC1.CN(C=O)C>O.C(OCC)(=O)C>[CH3:26][O:25][C:17]1[C:18]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:2]2[C:3]([C:4](=[O:5])[N:6]([CH2:7][CH2:8][C:9]3[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=3)[C:27](=[S:28])[NH:1]2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6348Carbon DisulfideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19363469HCID 19363469, compound

Product 1

HCID 19363314HCID 19363314, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-4-methoxy-3-pentyloxy-N-(2-pyridin-4-ylethyl)benzamide (200 mg, 0.560 mmol) obtained in Example 2-61, carbon disulfide (0.6 ml), 1,8-diazabicyclo [5.4.0]-7-undecene (0.0837 ml, 0.56 mmol) and DMF (1.0 ml) were mixed, and this mixture was refluxed under heating for 4 hours. Ethyl acetate (4 ml) and water were added to this reaction mixture. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (5 ml) and saturated brine (5 ml), and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to column chromatography on silica gel (chloroform/methanol=10/1) and recryst alli ztion from ethyl acetate to give 7-methoxy-8-pentyloxy-3-(2-pyridin-4-ylethyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one (24 mg, 11%) as colorless crystals.

Workup

  1. temperaturethis mixture was refluxed
  2. temperatureunder heating for 4 hours
  3. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (5 ml) and saturated brine (5 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5ff8e5217c8245edbf08feca52ac2407
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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