1,2,2-Trimethylpropyl isothiocyanate → N-(6-carbamoyl-3-pyridyl)-N'-(1,2,2-trimethylpropyl)thiourea

HRID 257424Notes

Reaction equation

HRID 257424 reaction equation
[C:1]([NH-:4])(O)=[O:2].[NH2:5][C:6]1[CH:7]=[N:8][C:9](CC(N)=O)=[CH:10][CH:11]=1.[CH3:16][CH:17]([N:22]=[C:23]=[S:24])[C:18]([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[C:1]([C:9]1[N:8]=[CH:7][C:6]([NH:5][C:23]([NH:22][CH:17]([CH3:16])[C:18]([CH3:21])([CH3:20])[CH3:19])=[S:24])=[CH:11][CH:10]=1)(=[O:2])[NH2:4]

Participants

5

Reactant 3

HCID 149751901,2,2-Trimethylpropyl isothiocyanateHCID 687181332-(5-Aminopyridin-2-yl)acetamideHCID 178514242HCID 178514242, compound

Product 1

HCID 9993833N-(6-carbamoyl-3-pyridyl)-N'-(1,2,2-trimethylpropyl)thioureaYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The carboxyamide compound (0.37 g, 27 mmol) obtained in (a) described above and 1,2,2-trimethylpropyl isothiocyanate (1.15 g, 8.03 mmol) were added to 2 ml of DMF, followed by reaction at 80°-90° C. for about 40 hours. DMF was removed by distillation, and the residue was purified by silica gel column chromatography (eluent: chloroform: methanol=13:1 (v/v)). Recrystallization from methanol-ether gave 0.4 g of the intended product (yield: 53%).

Workup

  1. customfollowed by reaction at 80°-90° C. for about 40 hours
  2. customDMF was removed by distillation
  3. customthe residue was purified by silica gel column chromatography (eluent: chloroform: methanol=13:1 (v/v))
  4. customRecrystallization from methanol-ether

Sources & evidence

ORD record
ord-4792e41ba7e44497b2f3ed6a917214b5
Source dataset
uspto-grants-1993_11
Patent number
US05262415

Reaction notes

Loading…