Dimethylformamide → HCID 18700166, compound

HRID 1740585Notes

Reaction equation

HRID 1740585 reaction equation
[C:1]([C:5]([N:7]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[C:16]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])[CH:15]=1)[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])=[O:6])([CH3:4])([CH3:3])[CH3:2].[C-:28]#N.[Na+].[CH3:31][N:32]([CH:34]=O)C>>[C:1]([C:5]([N:7]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18][C:31]#[N:32])=[C:16]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])[CH:15]=1)[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])=[O:6])([CH3:4])([CH3:3])[CH3:2].[C:1]([C:5]([NH:7][C:14]1[CH:21]=[CH:20][C:17]([CH2:28][C:34]#[N:32])=[C:16]([O:22][CH2:23][C:24]([F:26])([F:27])[F:25])[CH:15]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 18700073HCID 18700073, compound

Product 2

HCID 18700096HCID 18700096, compoundHCID 18700166HCID 18700166, compoundYield 15%

Procedure

To a stirred solution of 4-(N,N-di-(tert-butyl-carbonyl)-amino)-2-(2,2,2-trifluoroethoxy)benzyl bromide (1.5 g, 3.2 mmol) from Step 4 above in DMF (20 mL) was added NaCN (0.23 g, 4.8 mmol). The mixture was stirred at ambient temperature for 24 h. The solvent was removed under reduced pressure and the residue was purified by pressurized silica gel column chromatography using 15% EtOAc:hexanes as eluant to give an inseparable mixture (~3:1) of 4-(N,N-di-(tert-butylcarbonyl)amino)-2-(2,2,2-trifluoroethoxy)phenyl-acetonitrile and 4-(tert-butylcarbonylamino)-2-(2,2,2-trifluoroethoxy)-phenylacetonitrile (TLC Rf =0.28 (15% EtOAc:hexanes)).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-bb3662928aba4c40b678fe6fda8079f6
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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