Hydrochloric Acid → 4-Chloro-7-methyl-1,2,3-triazino[4',5'-4,5]thiopheno[2,3-b]pyridine

HRID 1732918Notes

Reaction equation

HRID 1732918 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[S:4][C:3]=1[C:12]#[N:13].[ClH:14].[N:15]([O-])=O.[Na+]>O>[Cl:14][C:12]1[C:3]2[S:4][C:5]3[N:6]=[C:7]([CH3:11])[CH:8]=[CH:9][C:10]=3[C:2]=2[N:1]=[N:15][N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7023133-Amino-6-methylthieno[2,3-b]pyridine-2-carbonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 4607114-Chloro-7-methyl-1,2,3-triazino[4',5'-4,5]thiopheno[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cold solution of 4.2 g. (0.022 M) of 3-amino-2-cyano-6-methylthieno[2,3-b]pyridine in 30 ml. conc. HCl and 30 ml. HOAC was added a solution of 1.9 g. (0.028 M) of NaNO2 in 20 ml. of H2O. After completion of addition, the ice bath was removed and stirring continued for 2 more hours. The mixture was then poured on ice water and filtered. The crude product was recrystallized from methanol, m.p. 188°-189° C.

Workup

  1. additionHOAC was added a solution of 1.9 g
  2. additionAfter completion of addition
  3. customthe ice bath was removed
  4. additionThe mixture was then poured on ice water
  5. filtrationfiltered
  6. customThe crude product was recrystallized from methanol, m.p. 188°-189° C.

Sources & evidence

ORD record
ord-c7dec922fb38482a83ffab16ba59e992
Source dataset
uspto-grants-1980_12
Patent number
US04239887

Reaction notes

Loading…