Hydrazine → HCID 71516761, compound

HRID 2173666Notes

Reaction equation

HRID 2173666 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:13])=[C:8]([Cl:12])[C:9]=2[CH3:11])[S:4][C:3]=1[C:14]#[N:15].[NH2:16][NH2:17]>CS(C)=O>[Cl:12][C:8]1[C:9]([CH3:11])=[C:10]2[C:2]3[NH:16][N:17]=[C:14]([NH2:15])[C:3]=3[S:4][C:5]2=[N:6][C:7]=1[CH3:13]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 89443875HCID 89443875, compound

Product 1

HCID 71516761HCID 71516761, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The 3-bromo-5-chloro-4,6-dimethylthieno[2,3-b]pyridine-2-carbonitrile (0.273 g, 0.91 mmol) was added to a microwave reaction vial. The DMSO (4 mL) was added, followed by hydrazine (0.085 mL, 2.72 mmol). The vial was sealed and irradiated at 120 degrees for 10 minutes. LC\MS shows no remaining starting material. The reaction was cooled to RT, then poured into 50 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 220 mg (96%) of the product as a light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 5.53 (bs, 2H), 2.74 (s, 3H), 2.61 (s, 3H). LC/MS: RT=0.58 min., m/z=253.0 [M+H]+.

Workup

  1. customThe vial was sealed
  2. customirradiated at 120 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-d0926edd198344e9a64e28eb5de42479
Source dataset
uspto-grants-2015_06
Patent number
US09056876B2

Reaction notes

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