Cyanamide → HCID 178464579, compound

HRID 1491649Notes

Reaction equation

HRID 1491649 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-6eef78f01f3243208128d848a4c3baa4
Source dataset
uspto-grants-1994_12
Patent number
US05371086

Reaction notes

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