Acetic Acid → HCID 13116412, compound

HRID 2295716Notes

Reaction equation

HRID 2295716 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:16]([O:18]CC)=[O:17])=[C:6]1[S:15][CH2:14][CH2:13][N:7]12.C(O)C.O.C(O)(=O)C>[OH-].[Na+]>[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:16]([OH:18])=[O:17])=[C:6]1[S:15][CH2:14][CH2:13][N:7]12

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 962WaterHCID 13116409HCID 13116409, compound

Product 1

HCID 13116412HCID 13116412, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 6,7-dichloro-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylate (1.0 gram, 2.9 mmol) obtained in Example 3 was suspended in a mixture of 2.0 grams of sodium hydroxide, 140 ml of ethanol and 60 ml of water, the mixture was heated to reflux for thirty minutes, acidified with acetic acid when it was still hot, crystals separated out were collected by filtration, washed with water, and dried and recrystallized from dimethyl formamide to give 580 mg (62.8 percent) of the title compound. Melting point 305° to 310° C. (decomposition). Elementary analysis calculated as C12H7Cl2NO3S: C 45.59, H 2.23, N 4.43; Found: C 45.85, H 2.19, N 4.37.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for thirty minutes
  3. customcrystals separated out
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried
  7. customrecrystallized from dimethyl formamide

Sources & evidence

ORD record
ord-09fb22c0784a4152b82d30c5ec4724bf
Source dataset
uspto-grants-1984_01
Patent number
US04426381

Reaction notes

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