Dimethylformamide → HCID 18700166, compound

HRID 2289330Notes

Reaction equation

HRID 2289330 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-butylcarbonyl)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-0ebb6b29d76f4f288fd03fcdcb17329c
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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