3,4-Diaminopyridine → HCID 67849427, compound

HRID 1491643Notes

Reaction equation

HRID 1491643 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[CH3:9][S:10][C:11](SC)=[CH:12][N+:13]([O-:15])=[O:14]>CN(C=O)C.C(N(CC)CC)C>[NH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:1][C:11]([S:10][CH3:9])=[CH:12][N+:13]([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 59183,4-DiaminopyridineHCID 836231,1-Bis(methylthio)-2-nitroethylene

Product 1

HCID 67849427HCID 67849427, compoundYield 13.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

3,4-Diaminopyridine (6.00 g, 55.0 mmol) and 1,1-bis(methylthio)-2-nitroethylene (10.0 g, 60.5 mmol) were dissolved in 60 ml of DMF and 10 ml of triethylamine, followed by reaction at 70° C. for 5 hours. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography [eluent: chloroform:methanol=2:1 (v/v)] to obtain 1.63 g of the intended product (yield: 13.1%)

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. customthe residue was purified by silica gel column chromatography [eluent: chloroform:methanol=2:1 (v/v)]

Sources & evidence

ORD record
ord-805516621c454ced8608e044dade321e
Source dataset
uspto-grants-1994_12
Patent number
US05371086

Reaction notes

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