Methylamine → 5-methyl-6,7-difluoro-1H,4H-thiazolo[3,4-a]quinoxaline-1-thione

HRID 1085309Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[C:10]=2F)[C:5](=[S:8])[S:6][CH:7]=1.[CH3:18][NH2:19]>C(#N)C.CO>[CH3:18][N:19]1[C:10]2[C:9](=[CH:14][CH:13]=[C:12]([F:15])[C:11]=2[F:16])[N:4]2[C:5](=[S:8])[S:6][CH:7]=[C:3]2[CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

4-Chloromethyl-3-(2,3,4-trifluorophenyl)-2(3H)thiazolethione (2.5 g) prepared in the same manner as in Reference Example 7 was dissolved in acetonitrile (25 ml) and to the solution was added 40 % solution of methylamine in methanol (3.3 g) and the mixture was stirred at 50° C. for 16 hours. The reaction mixture was evaporated to dryness under reduced pressure and to the residue was added water and the solution was extracted with chloroform. The extract was washed with a NaCl solution, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The obtained residue was recrystallized from a mixed solvent of cyclohexane - ethyl acetate to give the title compound (2.0 g) as pale yellow crystals, m.p. 165°-167° C.

Workup

customThe reaction mixture was evaporated to dryness under reduced pressure and to the residue
additionwas added water
extractionthe solution was extracted with chloroform
washThe extract was washed with a NaCl solution
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe obtained residue was recrystallized from a mixed solvent of cyclohexane - ethyl acetate

Sources & evidence

ORD record: ord-0d63e24e71e6413d82149b8c1c9b4e92
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05008389

Reaction notes

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