Methyl isothiocyanate → 2-Amino-5-(methyl-thiocarbamoyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

HRID 1732018Notes

Reaction equation

HRID 1732018 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]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 135196874H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridin-2-amine

Product 1

HCID 135196882-Amino-5-(methyl-thiocarbamoyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridineYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. temperaturethe solution was cooled in an ice-water bath
  2. customAfter 71/2 hours the solvent was removed by evaporation
  3. 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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