Acetic Acid → HCID 13116422, compound

HRID 2295722Notes

Reaction equation

HRID 2295722 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=[O:22])[C:7]([C:17]([O:19]CC)=[O:18])=[C:8]4[S:16][CH2:15][CH2:14][N:9]43)=[CH:4][C:3]=2[O:2]1.C(O)C.O.C(O)(=O)C>[OH-].[Na+]>[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=[O:22])[C:7]([C:17]([OH:19])=[O:18])=[C:8]4[S:16][CH2:15][CH2:14][N:9]43)=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 962WaterHCID 13116421HCID 13116421, compound

Product 1

HCID 13116422HCID 13116422, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 7,8-methylenedioxy-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a) quinoline-4-carboxylate (1.38 grams, 4.3 mmol) was suspended in a mixture of 2.0 grams of sodium hydroxide, 40 ml of ethanol and 30 ml of water and the whole mixture was heated to reflux for thirty minutes. Then it was acidified with acetic acid when the solution was still hot, the crystals separated out were collected by filtration, washed with water and air dried and the resulting crude crystals were recrystallized from dimethyl formamide to give 870 mg (69.0 percent) of the title compound, melting point 315° to 320° C. (decomposition). Elementary analysis calculated as C13H9NO5S: C 53.61, H 3.11, N 4.81; Found: C 53.68, H 2.92, N 4.66.

Workup

  1. temperaturethe whole mixture was heated
  2. temperatureto reflux for thirty minutes
  3. customthe crystals separated out
  4. filtrationwere collected by filtration
  5. washwashed with water and air
  6. customdried
  7. customthe resulting crude crystals were recrystallized from dimethyl formamide

Sources & evidence

ORD record
ord-cb2b12cae15e431491d0c953ceb5a69e
Source dataset
uspto-grants-1984_01
Patent number
US04426381

Reaction notes

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