Sodium hydride → HCID 21527078, compound

HRID 1659135Notes

Reaction equation

HRID 1659135 reaction equation
[OH:1][CH:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:5](=[O:13])[C:4]2[S:14][CH2:15][CH2:16][S:17][C:3]1=2.[H-].[Na+].Cl[C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]1)=[O:22]>O1CCCC1>[CH3:29][N:26]1[CH2:27][CH2:28][N:23]([C:21]([O:13][CH:5]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=3)[C:2](=[O:1])[C:3]3[S:17][CH2:16][CH2:15][S:14][C:4]2=3)=[O:22])[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 30169354-Methyl-1-piperazinecarbonyl chlorideHCID 21527053HCID 21527053, compound

Product 1

HCID 21527078HCID 21527078, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 5-hydroxy-7-oxo-6-(pyrid-2-yl)-2,3,6,7-tetrahydro-1,4-dithiino[2,3-c]pyrrole (6.0 g.) in anhydrous tetrahydrofuran (60 cc.) is treated for 17 minutes at about 5°-10°C, with sodium hydride (0.64 g.), and a solution of 1-chlorocarbonyl-4-methylpiperazine (11.0 g.) in anhydrous tetrahydrofuran (80 cc.) is then added, at 5°C. The reaction mixture is stirred for 4 hours at 5°C. After evaporating the solvent under reduced pressure (20 mm.Hg), the residue is dissolved in diethyl ether (300 cc.). The diethyl ether solution is washed three times with N sodium hydroxide solution (total 450 cc.) and then three times with distilled water (total 300 cc.), treated with vegetable charcoal (0.1 g.), dried over anhydrous potassium carbonate, filtered and evaporated. The residue (7.6 g.; m.p. 145°C.) is dissolved in boiling ethanol (20 cc.). After being cooled for two hours at 2°C, the crystals which have appeared are filtered off, washed twice with ice-cold ethanol (total 12 cc.) and dried under reduced pressure (20 mm.Hg). 5-(4-Methylpiperazin-1-yl)carbonyloxy-7-oxo-6-(pyrid-2-yl)-2,3,6,7-tetrahydro-1,4-dithiino[2,3-c]pyrrole (3.9 g.), melting at 150°C, is thus obtained.

Workup

  1. customAfter evaporating the solvent under reduced pressure (20 mm.Hg)
  2. dissolutionthe residue is dissolved in diethyl ether (300 cc.)
  3. washThe diethyl ether solution is washed three times with N sodium hydroxide solution (total 450 cc.)
  4. additionthree times with distilled water (total 300 cc.), treated with vegetable charcoal (0.1 g.)
  5. dry with materialdried over anhydrous potassium carbonate
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe residue (7.6 g.; m.p. 145°C.) is dissolved
  9. temperatureAfter being cooled for two hours at 2°C
  10. filtrationthe crystals which have appeared are filtered off
  11. washwashed twice with ice-cold ethanol (total 12 cc.)
  12. customdried under reduced pressure (20 mm.Hg)

Sources & evidence

ORD record
ord-d0447bef78e74dadad583957ca7bf33d
Source dataset
uspto-grants-1976_06
Patent number
US03966931

Reaction notes

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