Chloroacetonitrile → 3-Amino-6-methylthieno[2,3-b]pyridine-2-carbonitrile

HRID 1732917Notes

Reaction equation

HRID 1732917 reaction equation
[SH:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[C:4]([CH3:10])[N:3]=1.C[O-].[Na+].Cl[CH2:15][C:16]#[N:17]>CO>[NH2:9][C:8]1[C:7]2[C:2](=[N:3][C:4]([CH3:10])=[CH:5][CH:6]=2)[S:1][C:15]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 10942334Sodium MethoxideHCID 178425618HCID 178425618, compound

Product 1

HCID 7023133-Amino-6-methylthieno[2,3-b]pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 7.5 g. (0.05 mole) of 2-mercapto-3-cyano-6-methylpyridine in 200 ml. of MeOH was added 5.4 g. (0.1 M) sodium methoxide. Stirring was continued until all dissolved. 8.0 g. (0.1 M) of chloroacetonitrile in 20 ml. methanol was then added and the mixture was refluxed for 6 hours. After removal of the solvent, the residue was diluted with water and filtered. The crude product was crystallized from methanol, m.p. 241°-242° C. (Offin No. 2,241,717 in 3/4/74 reported m.p. 241°-243°).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customAfter removal of the solvent
  3. additionthe residue was diluted with water
  4. filtrationfiltered
  5. customThe crude product was crystallized from methanol, m.p. 241°-242° C. (Offin No. 2,241,717 in 3/4/74 reported m.p. 241°-243°)

Sources & evidence

ORD record
ord-dd319e3988c044358deb8d138d602980
Source dataset
uspto-grants-1980_12
Patent number
US04239887

Reaction notes

Loading…