Methyl isothiocyanate → 2-Amino-5-(methyl-thiocarbamoyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine
Reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:5][NH:6][CH2:7][CH2:8][C:9]=2[N:10]=1.[CH3:11][N:12]=[C:13]=[S:14]>CN(C)C=O>[NH2:1][C:2]1[S:3][C:4]2[CH2:5][N:6]([C:13](=[S:14])[NH:12][CH3:11])[CH2:7][CH2:8][C:9]=2[N:10]=1Participants
4
Procedure
1.55 G (10 mmol) of 2-amino-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine was dissolved in 25 ml of dimethylformamide and the solution was cooled in an ice-water bath. 0.88 g (12 mmol) of methyl isothiocyanate was then added. After 71/2 hours the solvent was removed by evaporation and the residue (about 2.2 g) was crystallized from acetonitrile. 1.25 g (55% yield) of the pure title compound (m.p. 188°-190° C. with decomposition) were obtained.
Workup
- temperaturethe solution was cooled in an ice-water bath
- customAfter 71/2 hours the solvent was removed by evaporation
- customthe residue (about 2.2 g) was crystallized from acetonitrile
Sources & evidence
- ORD record
- ord-f32c17a8c4d746dab4300c85204a2adb
- Source dataset
- uspto-grants-1986_11
- Patent number
- US04624956
Reaction notes
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