Guanidine Hydrochloride → HCID 178454308, compound

HRID 1875061Notes

Reaction equation

HRID 1875061 reaction equation
[C:1](OC([O-])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[NH2:13][C:14]([NH2:16])=[NH:15].[OH-].[Na+]>CC(C)=O.O>[NH2:15][C:14]([NH:16][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[NH:13]

Participants

6

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 14798Sodium HydroxideHCID 22064466Tert-butyldicarbonate

Product 1

HCID 178454308HCID 178454308, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of tert-butyl dicarbonate (57.3 g, 263 mmol) in acetone (500 mL) was added to a solution of guanidine hydrochloride (100 g, 1050 mmol) and sodium hydroxide (84 g, 2100 mmol) in water (400 mL) at 0° C. The mixture was stirred at RT for 2 hrs. The acetone was removed by rotary evaporation and the remaining suspension was extracted with EtOAc (3×). The combined organic layers were dried over sodium sulfate and the solvent was evaporated to give 1,1-dimethylethyl [amino(imino)methyl]carbamate (42 g, 100%). 1H NMR (400 MHz, chloroform-d) δ ppm 6.08 (br. s., 4H), 1.44 (s, 9H).

Workup

  1. customThe acetone was removed by rotary evaporation
  2. extractionthe remaining suspension was extracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-17261cd3489a4045a808881b83f990f8
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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