Tetrahydrofuran → HCID 15136147, compound

HRID 1651046Notes

Reaction equation

HRID 1651046 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].O1CCCC1.[NH:14]1[CH2:19][CH2:18][S:17][CH2:16][CH2:15]1.[CH2:20]([O:22][C:23]([C:25]1[C:34](=[O:35])[N:33]2[C:28]([C:29]([SH:36])=[CH:30][CH:31]=[CH:32]2)=[CH:27][CH:26]=1)=[O:24])[CH3:21]>C(N(CC)CC)C>[CH2:20]([O:22][C:23]([C:25]1[C:34](=[O:35])[N:33]2[C:28]([C:29]([S:36][C:2]([N:14]3[CH2:19][CH2:18][S:17][CH2:16][CH2:15]3)=[O:3])=[CH:30][CH:31]=[CH:32]2)=[CH:27][CH:26]=1)=[O:24])[CH3:21]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10426DiphosgeneHCID 67164ThiomorpholineHCID 15136157HCID 15136157, compound

Product 1

HCID 15136147HCID 15136147, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.24 ml of trichloromethyl chloroformate (TCF) and 15 ml of tetrahydrofuran is stirred at 60° C. for 2 hours, cooled with ice, mixed with 412 mg of thiomorpholine, and the mixture is stirred for 1 hour at room temperature. The reaction mixture is cooled with ice again and mixed with 1.212 g of triethylamine. The mixture is stirred at room temperature for 1 hour, mixed with 500 mg of 3-ethoxycarbonyl-9-mercapto-4H-quinolizin-4-one (II-3), and the mixture is stirred at room temperature for 17 hours. The reaction mixture is filtered, and the filtrate is concentrated. The residue is chromatographed on a column of 10 g of silica gel, eluting with methylene chloride-methanol (19:1 v/v). The resultant crystals are recrystallized from ethyl acetate to give 321 mg (Yield: 42.3%) of 3-ethoxycarbonyl-9-(thiomorpholinocarbonylthio)-4H-quinolizin-4-one (I a-6).

Workup

  1. temperaturecooled with ice
  2. stirringthe mixture is stirred for 1 hour at room temperature
  3. temperatureThe reaction mixture is cooled with ice again
  4. stirringThe mixture is stirred at room temperature for 1 hour
  5. stirringthe mixture is stirred at room temperature for 17 hours
  6. filtrationThe reaction mixture is filtered
  7. concentrationthe filtrate is concentrated
  8. customThe residue is chromatographed on a column of 10 g of silica gel
  9. washeluting with methylene chloride-methanol (19:1 v/v)
  10. customThe resultant crystals are recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0c1981a65c08455381c14a890e346642
Source dataset
uspto-grants-1990_05
Patent number
US04927829

Reaction notes

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