Sodium hydride → 1-(4-chlorobutyl)-5,6-dihydro-(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide

HRID 654102Notes

Reaction equation

HRID 654102 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5]N1C2=C3C(=CC=C2)CCCN3S1.[NH:18]1[C:28]2=[C:29]3[C:24](=[CH:25][CH:26]=[CH:27]2)[CH2:23][CH2:22][CH2:21][N:20]3[S:19]1(=[O:31])=[O:30].[H-].[Na+].BrCCCCCl>CN(C)C=O.O.C(OCC)(=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:18]1[C:28]2=[C:29]3[C:24](=[CH:25][CH:26]=[CH:27]2)[CH2:23][CH2:22][CH2:21][N:20]3[S:19]1(=[O:30])=[O:31]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 156467015,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxideHCID 198884671-(4-Chlorobutyl)-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline

Product 1

HCID 198884521-(4-chlorobutyl)-5,6-dihydro-(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

1-(4-Chlorobutyl)-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline can be prepared as follows: a solution of 5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide (4 g) in dry N,N-dimethylformamide (20 cc) is added dropwise to a suspension of sodium hydride (0.69 g, 80% suspension in oil) in N,N-dimethylformamide (20 cc). After 30 minutes' stirring, a solution of 1-bromo-4-chlorobutane (3.93 g) in N,N-dimethylformamide (20 cc) is added. The reaction mixture is stirred at 20° C. for 2 hours and then diluted in a mixture of water (200 cc) and ethyl acetate (200 cc). The organic phase is washed with water (3×200 cc), is dried over magnesium sulphate and is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 50-cm height) and eluted at a pressure of 0.7 bars of nitrogen with a mixture of cyclohexane and ethyl acetate (80-20 by volume), 125-cc fractions being collected. Fractions 3 to 9 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give 1-(4-chlorobutyl)-5,6-dihydro-(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide (4.5 g).

Workup

  1. stirringThe reaction mixture is stirred at 20° C. for 2 hours
  2. washThe organic phase is washed with water (3×200 cc)
  3. dry with materialis dried over magnesium sulphate
  4. concentrationis concentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 50-cm height)
  6. washeluted at a pressure of 0.7 bars of nitrogen with a mixture of cyclohexane and ethyl acetate (80-20 by volume), 125-cc fractions
  7. custombeing collected
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-a6d0de2e28d94d92b26bf4ac51ba9aaf
Source dataset
uspto-grants-1992_07
Patent number
US05130313

Reaction notes

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