Cyanuric chloride → HCID 98007406, compound

HRID 1696210Notes

Reaction equation

HRID 1696210 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14](=O)[NH2:15])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].ClC1N=C(Cl)N=C(Cl)N=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]#[N:15])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 516892Sodium BicarbonateHCID 124155304HCID 124155304, compound

Product 1

HCID 98007406HCID 98007406, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl[trans-3-carbamoylcyclohexyl]-carbamate (180 mg) in N,N-dimethylformamide (2 ml) was added 2,4,6-trichloro-1,3,5-triazine (76 mg) under stirring at 0° C. After stirring at ambient temperature for 2 hours, the reaction mixture was poured into saturated aqueous sodium hydrogencarbonate, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography on silica gel with n-hexane:EtOAc=80:20-50:50 to give tert-butyl[trans-3-cyanocyclohexyl]carbamate (125 mg) as a white powder.

Workup

  1. stirringAfter stirring at ambient temperature for 2 hours
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel with n-hexane

Sources & evidence

ORD record
ord-f8bdcf4c6cd941f298ad6800e207a495
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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