Hydrochloric Acid → HCID 68870503, compound

HRID 2374860Notes

Reaction equation

HRID 2374860 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[N:5][C:6]([CH:9]([NH:11]C(=O)OC(C)(C)C)[CH3:10])=[CH:7][N:8]=1.[ClH:19]>CO.O1CCOCC1.C(OCC)(=O)C>[ClH:19].[CH3:1][S:2][C:3]1[N:4]=[N:5][C:6]([CH:9]([NH2:11])[CH3:10])=[CH:7][N:8]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 58711973HCID 58711973, compound2×

Product 1

HCID 68870503HCID 68870503, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl 1-[3-(methylthio)-1,2,4-triazin-6-yl]ethylcarbamate (Intermediate 3) (13.3 g, 49 mmol) in methanol (100 mL) was added 4N HCl in dioxane (50 mL). After stirring for 30 minutes the volatiles were removed under reduced pressure to provide a colorless oil. The oil was taken up in ethyl acetate, and the volatiles again removed under reduced pressure to give 1-[3-(methylthio)-1,2,4-triazin-6-yl]ethanamine hydrochloride (10.1 g) as a white solid. MS m/z 171 (M+1). A portion of the white solid (90 mg) was slurried in ethyl acetate and washed with saturated sodium bicarbonate solution causing the solid to dissolve. The volatiles were removed under reduced pressure to give 1-[3-(methylthio)-1,2,4-triazin-6-yl]ethanamine (68 mg) as a foam. MS m/z 171 (M+1).

Workup

  1. customwere removed under reduced pressure
  2. customto provide a colorless oil
  3. customthe volatiles again removed under reduced pressure

Sources & evidence

ORD record
ord-d61e9544f56545cd831793e22671b33e
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

Loading…