Hydrochloric Acid → Methyl(10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)acetimidate hydrochloride

HRID 1059452Notes

Reaction equation

HRID 1059452 reaction equation
[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15][C:16]#[N:17])[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1.[CH3:18][OH:19].[ClH:20]>ClCCl>[ClH:20].[CH3:18][O:19][C:16](=[NH:17])[CH2:15][C:12]1[CH:13]=[CH:14][C:7]2[S:6][C:5]3[N:4]=[CH:3][CH:2]=[N:1][C:10]=3[NH:9][C:8]=2[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1867021210H-Pyrazino[2,3-b][1,4]benzothiazine-8-acetonitrile

Product 1

HCID 131723771Methyl(10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)acetimidate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

480 mg of (10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)acetonitrile was suspended in a solution of dry methanol (20 ml)/dry dichloromethane and cooled to −20° C. Then dry hydrogen chloride gas was blown thereinto until saturation was attained while paying attention lest the bulk temperature exceed 0° C. Then the reaction mixture was hermetically sealed and allowed to stand under ice-cooling over day and night. Next, the solvent was distilled off under reduced pressure while maintaining the bulk temperature at room temperature or below. Then a small amount of dry methanol was added to the residue and ethyl acetate was gradually added thereto under ultrasonication. The orange crystals thus precipitated were taken up by filtration, washed with diethyl ether and dried under reduced pressure. Thus, 570 mg of the title compound was obtained.

Workup

  1. customexceed 0° C
  2. customThen the reaction mixture was hermetically sealed
  3. temperaturecooling over day and night
  4. distillationNext, the solvent was distilled off under reduced pressure
  5. temperaturewhile maintaining the bulk temperature at room temperature or below
  6. additionThen a small amount of dry methanol was added to the residue and ethyl acetate
  7. additionwas gradually added
  8. customunder ultrasonication
  9. customThe orange crystals thus precipitated
  10. filtrationwere taken up by filtration
  11. washwashed with diethyl ether
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-61387e11f28d48538a854ff641a882cd
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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