Cyanuric chloride → tert-Butyl ((1-(cyanomethyl)cyclohexyl)methyl)carbamate

HRID 722841Notes

Reaction equation

HRID 722841 reaction equation
N1C(Cl)=NC(Cl)=NC=1Cl.[C:10]([O:14][C:15](=[O:28])[NH:16][CH2:17][C:18]1([CH2:24][C:25](=O)[NH2:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)([CH3:13])([CH3:12])[CH3:11].CCCCCC.CCOC(C)=O>CN(C=O)C>[C:10]([O:14][C:15](=[O:28])[NH:16][CH2:17][C:18]1([CH2:24][C:25]#[N:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)([CH3:11])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 21226206Ethyl acetate hexaneHCID 53862491(1-Carbamoylmethyl-cyclohexylmethyl)-carbamic Acid tert-butyl Ester

Product 1

HCID 53643555tert-Butyl ((1-(cyanomethyl)cyclohexyl)methyl)carbamateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyanuric chloride (39.5 g, 0.214 mol) was added to (1-carbamoylmethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester (3) (116 g, 0.429 mol) in 400 mL DMF. An ice-water bath was used to moderate the exotherm, and the reaction mixture was stirred at room temperature for 1.5 hours. The mixture was poured into ice-water containing 120 g (1.43 mol) NaHCO3 and was extracted 4× EtOAc. The extracts were washed 1× water, 2× brine and dried over Na2SO4. Evaporation yielded an oil which was taken up in 3:1 hexane/EtOAc and filtered through silica gel. Evaporation yielded white crystals (86.5 g, 80%); mp 54–58° C.

Workup

  1. customAn ice-water bath was used
  2. extractionwas extracted 4× EtOAc
  3. washThe extracts were washed 1× water, 2× brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation
  6. customyielded an oil which
  7. filtrationfiltered through silica gel
  8. customEvaporation

Sources & evidence

ORD record
ord-c4a38d0f2bcc440ba6dd7b4faef6feeb
Source dataset
uspto-grants-2006_11
Patent number
US07138542B2

Reaction notes

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