Sodium Sulfide → 2,3-Dihydro-5,6-dimethyl-3-thioxo-4-pyridazinecarbonitrile

HRID 2173471Notes

Reaction equation

HRID 2173471 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([CH3:11])=[C:6]([CH3:10])[C:7]=1[C:8]#[N:9].[S-2:12].[Na+].[Na+]>C(O)(C)(C)C.CC(O)C>[CH3:10][C:6]1[C:5]([CH3:11])=[N:4][NH:3][C:2](=[S:12])[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 2

HCID 14804Sodium SulfideHCID 3340163-chloro-5,6-dimethylpyridazine-4-carbonitrile

Product 1

HCID 256489772,3-Dihydro-5,6-dimethyl-3-thioxo-4-pyridazinecarbonitrile

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 3-chloro-5,6-dimethylpyridazine-4-carbonitrile (100 mg, 0.60 mmol) and sodium sulfide was stirred in tert-butanol (2.0 mL) in a microwave reaction vial. The vial was sealed and irradiated at 100° C. for 10 minutes. LC/MS indicated product and no remaining starting material. The reaction solution was diluted with IPA (˜10 mL) and stirred at ambient temperature for about 15 minutes, then filtered. The solids on the filter were washed with IPA. The solute was concentrated in vacuo, and the resulting solid was dried overnight at 60° C. in a vacuum oven to give the product. LC/MS: RT=0.24 min., m/z=166 [M+H]+.

Workup

  1. customThe vial was sealed
  2. customirradiated at 100° C. for 10 minutes
  3. filtrationfiltered
  4. washThe solids on the filter were washed with IPA
  5. concentrationThe solute was concentrated in vacuo
  6. customthe resulting solid was dried overnight at 60° C. in a vacuum oven
  7. customto give the product

Sources & evidence

ORD record
ord-3fae2a5ebada431f88ff1cc573fdb09b
Source dataset
uspto-grants-2015_06
Patent number
US09056875B2

Reaction notes

Loading…