Cyanuric chloride → HCID 57916539, compound

HRID 1040496Notes

Reaction equation

HRID 1040496 reaction equation
[CH2:1]([O:8][C:9](=[O:17])[NH:10][C:11]1([C:14](=O)[NH2:15])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:17])[NH:10][C:11]1([C:14]#[N:15])[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 13676801(1-Carbamoyl-cyclopropyl)-carbamic acid benzyl ester

Product 1

HCID 57916539HCID 57916539, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of (1-carbamoyl-cyclopropyl)-carbamic acid benzyl ester (1.8 g, 7.7 mmol) in DMF (20 mL) was added cyanuric chloride in one portion. The reaction was allowed to warm to room temperature overnight. The reaction was quenched with water and extracted with EtOAc (3×100 mL). The combined extracts were washed with water (3×50 mL), brine and dried with MgSO4. The mixture was filtered and concentrated. The resulting crude residue was dissolved in 30% EtOAc in hexanes (90 mL) and filtered through a plug of silica gel. The filtrate was concentrated to give (1-cyano-cyclopropyl)-carbamic acid benzyl ester (1.4 g, 6.5 mmol) as a white foam.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined extracts were washed with water (3×50 mL), brine
  4. dry with materialdried with MgSO4
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated
  7. dissolutionThe resulting crude residue was dissolved in 30% EtOAc in hexanes (90 mL)
  8. filtrationfiltered through a plug of silica gel
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8dd9570f492d4028a1bf4af76aa5410e
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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