Potassium Carbonate → tert-butyl N-[1-(N'-hydroxycarbamimidoyl)-1-methylethyl]carbamate

HRID 927399Notes

Reaction equation

HRID 927399 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl-].[OH:8][NH3+:9].[C:10]([C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:14])[CH3:13])#[N:11]>O.C(O)C>[NH2:11]/[C:10](=[N:9]\[OH:8])/[C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21645Hydroxylamine HClHCID 18316698tert-butyl N-(1-cyano-1-methylethyl)carbamate

Product 1

HCID 61324195tert-butyl N-[1-(N'-hydroxycarbamimidoyl)-1-methylethyl]carbamateYield 94.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (3.64 g) was dissolved in water (12 mL) and hydroxylammonium chloride (CAN: 5470-11-1, 1.7 g, mmol) was added. A solution of tert-butyl 2-cyanopropan-2-ylcarbamate (4.84 g, 26 mmol) in ethanol (42 mL) was added and the resulting reaction mixture was stirred for 18 h at ambient temperature. The solvent was removed under reduced pressure and the residue was diluted with ethyl acetate (20 mL). The mixture was filtered and the filtrate was concentrated to yield the crude product (5 g, 87.6%) as yellow solid. MS: m/e=218.2 [M+H]+.

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue was diluted with ethyl acetate (20 mL)
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0e3f594268084b79bb1ec7a5ea1f9aa8
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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