Cyanamide → HCID 178464579, compound

HRID 257431Notes

Reaction equation

HRID 257431 reaction equation
[N:1]#[C:2][NH2:3].C(N(C(C)C)CC)(C)C.[CH3:13][S:14]([NH:17][C:18]1[N:23]=[CH:22][C:21]([N:24]=[C:25]=[N:26][CH:27]([CH3:32])[C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:20][CH:19]=1)(=[O:16])=[O:15]>C(Cl)(Cl)Cl>[CH3:13][S:14]([NH:17][C:18]1[N:23]=[CH:22][C:21]([NH:24][C:25]([NH:26][CH:27]([CH3:32])[C:28]([CH3:31])([CH3:30])[CH3:29])=[N:3][C:2]#[N:1])=[CH:20][CH:19]=1)(=[O:15])=[O:16]

Participants

5

Reactant 3

HCID 9864CyanamideHCID 81531DiisopropylethylamineHCID 18953576HCID 18953576, compound

Product 1

HCID 178464579HCID 178464579, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Cyanamide (172 mg, 4.1 mmol) and diisopropylethylamine (711 μl, 4.1 mmol) were added to 1 ml of a solution of N-(6-methanesulfonylamino-3-pyridyl)-N'-(1,2,2-trimethylpropyl)carbodiimide (121 mg, 0.41 mmol) in chloroform and the mixture was stirred at room temperature for 16 hours. After an insoluble matter was removed by filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography [eluent: chloroform alone to chloroform:methanol =5:1 (v/v)] and subjected to recrystallization from chloroform-ether to obtain 97 mg of the intended product (yield: 72%).

Workup

  1. customAfter an insoluble matter was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography [eluent
  4. customchloroform alone to chloroform:methanol =5:1 (v/v)] and subjected to recrystallization from chloroform-ether

Sources & evidence

ORD record
ord-327eef7d6da74df5beebbcc482406e02
Source dataset
uspto-grants-1993_11
Patent number
US05262415

Reaction notes

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