Hydrazine → HCID 71516705, compound

HRID 2173664Notes

Reaction equation

HRID 2173664 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:12])=[CH:8][C:9]=2[CH3:11])[S:4][C:3]=1[C:13]#[N:14].[NH2:15][NH2:16]>CS(C)=O>[CH3:12][C:7]1[N:6]=[C:5]2[S:4][C:3]3[C:13]([NH2:14])=[N:16][NH:15][C:2]=3[C:10]2=[C:9]([CH3:11])[CH:8]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 89443778HCID 89443778, compound

Product 1

HCID 71516705HCID 71516705, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The 3-bromo-4,6-dimethylthieno[2,3-b]pyridine-2-carbonitrile (1.11 g, 4.17 mmol) was added to a microwave reaction vial. The DMSO (14 mL) was added, followed by hydrazine (0.392 mL, 12.5 mmol). The vial was sealed and irradiated at 150 degrees for 10 minutes. LCMS showed no remaining starting material. The reaction was cooled to RT, then poured into 150 mL of ice-water. The ice was allowed to melt and resulting slurry was poured through filter paper, washing the solid with cold water (3×). The solid was then dried under vacuum at 60° C. to give 908 mg (98%) of the product as a light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.07 (s, 1H), 5.35 (bs, 2H), 2.62 (s, 3H), 2.49 (s, 3H). LC/MS: RT=0.38 min., m/z=219.0 [M+H]+.

Workup

  1. customThe vial was sealed
  2. customirradiated at 150 degrees for 10 minutes
  3. customresulting slurry
  4. additionwas poured
  5. filtrationthrough filter paper
  6. washwashing the solid with cold water (3×)
  7. customThe solid was then dried under vacuum at 60° C.

Sources & evidence

ORD record
ord-a4bfb462fea84b77bf3f9a9d32096cc6
Source dataset
uspto-grants-2015_06
Patent number
US09056876B2

Reaction notes

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