Ammonia → tert-butyl N-(1-carbamimidoylcyclopropyl)carbamate

HRID 1040463Notes

Reaction equation

HRID 1040463 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C:8]1([C:11]#[N:12])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[O-]CC.[Na+].[NH4+:18].[Cl-].N.CO>CCO>[C:1]([O:5][C:6](=[O:13])[NH:7][C:8]1([C:11](=[NH:18])[NH2:12])[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 887MethanolHCID 25517Ammonium ChlorideHCID 2723922Sodium ethoxideHCID 20825555tert-butyl N-(1-cyanocyclopropyl)carbamate

Product 1

HCID 58430989tert-butyl N-(1-carbamimidoylcyclopropyl)carbamateYield 109%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(1-Cyano-cyclopropyl)-carbamic acid tert-butyl ester (2.44 g, 13.40 mmol) was dissolved in dry EtOH (33 mL). Sodium ethoxide (21 wt % in EtOH solution, 10.70 mL, 22.80 mmol)) was added and the reaction was stirred for 1 h at room temperature under an atmosphere of dry argon. To the light yellow solution was added solid NH4Cl (2.94 g, 55 mmol) followed by 7 M NH3 in MeOH (8.08 mL, 56.60 mmol). The reaction was capped and allowed to stir for 16 h. The turbid suspension was filtered using MeOH to rinse. The filtrate was concentrated in vacuo and the solid residue was re-suspended in dry EtOH. The solids were filtered off, rinsing with EtOH. The filtrate was concentrated to give 2.91 g of (1-Carbamimidoyl-cyclopropyl)-carbamic acid tert-butyl ester as a light yellow solid. m/z 200.48 [M+1]+

Workup

  1. customThe reaction was capped
  2. stirringto stir for 16 h
  3. filtrationThe turbid suspension was filtered
  4. washto rinse
  5. concentrationThe filtrate was concentrated in vacuo
  6. filtrationThe solids were filtered off
  7. washrinsing with EtOH
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-373987b60a034396b7874d2d38168718
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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