Sodium hydride → HCID 21527037, compound

HRID 1604962Notes

Reaction equation

HRID 1604962 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]([OH:15])[C:13]3[S:16][CH2:17][CH2:18][S:19][C:12]=3[C:11]2=[O:20])=[N:8][CH:9]=1.Cl[C:22]([N:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH3:31])[CH2:26][CH2:25]1)=[O:23]>O1CCCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:11]([O:20][C:22]([N:24]3[CH2:29][CH2:28][N:27]([CH2:30][CH3:31])[CH2:26][CH2:25]3)=[O:23])[C:12]3[S:19][CH2:18][CH2:17][S:16][C:13]=3[C:14]2=[O:15])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10559194HCID 10559194, compoundHCID 21527081HCID 21527081, compound

Product 1

HCID 21527037HCID 21527037, compoundYield 28.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A suspension of sodium hydride (1.11 g.) in anhydrous tetrahydrofuran (120 cc.) is treated for 20 minutes at about 10°-15° C. with 6-(5-chloropyrid-2-yl)-5-hydroxy-7-oxo-2,3,6,7-tetrahydro-1,4-dithiino[2,3-c]pyrrole (11.6 g.), and a solution of 1-chlorocarbonyl-4-ethylpiperazine (20.4 g.) in anhydrous tetrahydrofuran (160 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 (400 cc.). The ether solution is washed twice with ice-cold normal sodium hydroxide solution (total 300 cc.) and three times with distilled water (total 300 cc.), treated with decolourising charcoal (0.2 g.), dried over anhydrous sodium sulphate, filtered and evaporated. The residue (13.8 g.; m.p. 140° C.) is dissolved in boiling ethanol (25 cc.). After cooling for 3 hours at 2° C, the crystals which have appeared are filtered off, washed twice with ice-cold ethanol (total 20 cc.) and dried under reduced pressure (20 mm. Hg). 6-(5-Chloropyrid-2-yl)-5-(4-ethylpiperazin-1-yl)carbonyloxy-7-oxo-2,3,6,7-tetrahydro-1,4-dithiino[2,3-c]pyrrole (4.9 g.), melting at 163° C, is thus obtained.

Workup

  1. customAfter evaporating the solvent under reduced pressure (20 mm. Hg)
  2. dissolutionthe residue is dissolved in diethyl ether (400 cc.)
  3. washThe ether solution is washed twice with ice-cold normal sodium hydroxide solution (total 300 cc.) and three times with distilled water (total 300 cc.)
  4. additiontreated with decolourising charcoal (0.2 g.)
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe residue (13.8 g.; m.p. 140° C.) is dissolved
  9. temperatureAfter cooling for 3 hours at 2° C
  10. filtrationthe crystals which have appeared are filtered off
  11. washwashed twice with ice-cold ethanol (total 20 cc.)
  12. customdried under reduced pressure (20 mm. Hg)

Sources & evidence

ORD record
ord-55e92b747ab54cec882bb269d1197c93
Source dataset
uspto-grants-1976_04
Patent number
US03948917

Reaction notes

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