Trichloroacetonitrile → HCID 86672614, compound

HRID 470709Notes

Reaction equation

HRID 470709 reaction equation
N12CCCN=C1CCCCC2.[Si:12]([O:19][CH2:20][C@H:21]1[O:27][C@H:25]([CH3:26])[CH:24]=[CH:23][C@@H:22]1[OH:28])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[Cl:29][C:30]([Cl:34])([Cl:33])[C:31]#[N:32]>ClCCl>[Si:12]([O:19][CH2:20][C@H:21]1[O:27][C@H:25]([CH3:26])[CH:24]=[CH:23][C@@H:22]1[O:28][C:31](=[NH:32])[C:30]([Cl:34])([Cl:33])[Cl:29])([C:15]([CH3:17])([CH3:18])[CH3:16])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 70871896HCID 70871896, compound

Product 1

HCID 86672614HCID 86672614, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (1.00 ml, 6.83 mmol) was added to a dichloromethane (22 ml) solution of the compound (6.83 mmol) obtained in Step 2 above combined with trichloroacetonitrile (0.82 ml, 8.20 mmol) under ice cooling and the resulting mixture was stirred at room temperature for 1 hour. The solvent in the reaction mixture was evaporated under reduced pressure and the residue was dissolved in chloroform and added dropwise into n-hexane:ethyl acetate [4:1 (v/v)] mixed solvent. The resulting insoluble matter was removed by filtration through celite and the solvent in the filtrate was evaporated under reduced pressure. The residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=99:1→10:1 (v/v)] to give 2.1 g (77%) of the title compound as a colorless oil.

Workup

  1. customThe solvent in the reaction mixture was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. additionadded dropwise into n-hexane
  4. additionethyl acetate [4:1 (v/v)] mixed solvent
  5. customThe resulting insoluble matter was removed by filtration through celite
  6. customthe solvent in the filtrate was evaporated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=99:1→10:1 (v/v)]

Sources & evidence

ORD record
ord-59b6e4bd919546cda8e1451d3ef7686d
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

Loading…