Reaction #1127653

Reaction equation

NH4Cl

(1-Cyano-cyclopropyl)-carbamic acid tert-butyl ester

NaOEt

NH3

NaOEt

→

title compound

Yield 81.2%

(1-Carbamimidoyl-cyclopropyl)-carbamic acid tert-butyl ester hydrochloride

Yield 81.2%

Solvents

EtOH

Conditions

Workup

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 2 h
3. 3
   OtherThe flask was sealed
4. 4
   workup.STIRRINGto stir for 88 h
5. 5
   FiltrationThe solids were filtered off
6. 6
   Washto rinse
7. 7
   ConcentrationThe filtrate was concentrated
8. 8
   TemperatureThis mixture was heated
9. 9
   Temperatureto reflux for 30 min
10. 10
    Temperatureto cool to room temperature
11. 11
    FiltrationThe solids were collected by filtration

Procedure

(1-Cyano-cyclopropyl)-carbamic acid tert-butyl ester (2.12 g, 11.6 mmol) was dissolved in anhydrous EtOH (29 mL) and NaOEt (21 wt % in EtOH, 6.5 mL, 17.5 mmol) was added via syringe in one portion. The yellow solution was stirred at room temperature for 1 h. An additional amount of NaOEt (21 wt % in EtOH, 2.2 mL, 2.9 mmol) was added and stirring was continued for 2 h. To the reaction was added solid NH4Cl (2.5 g, 47 mmol) followed by NH3 (7N in MeOH, 1.7 mL, 12 mmol). The flask was sealed and the suspension was allowed to stir for 88 h. The solids were filtered off, using anhydrous EtOH to rinse. The filtrate was concentrated and re-suspended in EtOAc (10 mL). This mixture was heated to reflux for 30 min then allowed to cool to room temperature. The solids were collected by filtration to give 2.22 g of the title compound as a white powder, m/z 200.44 [M+1]+.

Source