Hydrochloric Acid → HCID 86755474, compound

HRID 1422224Notes

Reaction equation

HRID 1422224 reaction equation
C([O-:3])C.[Na+].[CH2:5]([O:7][C:8](=[O:11])[CH2:9][SH:10])[CH3:6].[Br:12][C:13]1[CH:22]=[C:21]2[C:16]([N:17]=[C:18]([O:25]C)[C:19](OC)=[N:20]2)=[C:15]([CH2:27]Br)[CH:14]=1.Cl>C(O)C.O1CCCC1>[CH2:5]([O:7][C:8](=[O:11])[C:9]([S:10][CH2:27][C:15]1[CH:14]=[C:13]([Br:12])[CH:22]=[C:21]2[C:16]=1[NH:17][C:18](=[O:25])[CH2:19][NH:20]2)=[O:3])[CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxideHCID 23298010HCID 23298010, compound

Product 1

HCID 86755474HCID 86755474, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

1.5 ml (4 mmol) of a 21% solution of sodium ethanolate in ethanol are diluted with 10 ml of ethanol under nitrogen. 601 mg (5 mmol) of thioglycolic acid ethyl ester are added at 0° C. and the mixture is heated to 20° C. After one hour, 1.09 g (3 mmol) of 7-bromo-5-bromomethyl-2,3-dimethoxy-quinoxaline, 10 ml of ethanol and 10 ml of tetrahydrofuran are added. The mixture is stirred for 18 hours, acidified with 2 ml of 2N hydrochloric acid and concentrated by evaporation. The residue is extracted with ethyl acetate and 0.1N hydrochloric acid, and the combined organic phases are washed with 10% sodium carbonate solution and brine, dried over magnesium sulfate and concentrated by evaporation. The residue is dissolved in 20 ml of a 33% solution of hydrogen bromide in acetic acid, and the solution is heated at 130° C. for 20 minutes and cooled to approximately 80° C. 20 ml of ethanol are added with stirring and the solution is left to stand at 5° C. for 18 hours. The crystals are filtered off, washed with cold ethanol and dried.

Workup

  1. concentrationconcentrated by evaporation
  2. extractionThe residue is extracted with ethyl acetate and 0.1N hydrochloric acid
  3. washthe combined organic phases are washed with 10% sodium carbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. dissolutionThe residue is dissolved in 20 ml of a 33% solution of hydrogen bromide in acetic acid
  7. temperaturethe solution is heated at 130° C. for 20 minutes
  8. temperaturecooled to approximately 80° C
  9. addition20 ml of ethanol are added
  10. stirringwith stirring
  11. waitthe solution is left
  12. waitto stand at 5° C. for 18 hours
  13. filtrationThe crystals are filtered off
  14. washwashed with cold ethanol
  15. customdried

Sources & evidence

ORD record
ord-bed3ad5e84694e8292696030ed1e4cbe
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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