Cyanuric chloride → tert-butyl N-(1-cyanocyclopropyl)carbamate

HRID 586133Notes

Reaction equation

HRID 586133 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1([C:11](=O)[NH2:12])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1([C:11]#[N:12])[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 20825554tert-butyl N-(1-carbamoylcyclopropyl)carbamate

Product 1

HCID 20825555tert-butyl N-(1-cyanocyclopropyl)carbamateYield 53.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (1-carbamoyl-cyclopropyl)-carbamic acid tert-butyl ester (5.7 g, 28.4 mmol) in DMF (50 mL) was added cyanuric chloride (2.6 g, 14.2 mmol) and it was stirred at room temperature for 1 h before it was diluted with water (400 mL). The product precipitated and filtration gave (1-cyano-cyclopropyl)-carbamic acid tert-butyl ester (2.79 g, 53.9%).

Workup

  1. customThe product precipitated
  2. filtrationfiltration

Sources & evidence

ORD record
ord-d1d8680fe973410481f5015b533c5343
Source dataset
uspto-grants-2005_08
Patent number
US06936606B2

Reaction notes

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