Dimethylformamide → HCID 20536520, compound

HRID 1156103Notes

Reaction equation

HRID 1156103 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[H][H].C[N:33](C)C=O>>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH:33][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8208Myristyl bromideHCID 24758Sodium hydride2×HCID 67975Benzoic acid, 3-fluoro-, ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 20536520HCID 20536520, compound

Procedure

To a solution of 16.5 g of ethyl 3-fluorobenzoate in 150 ml. of dry N,N-dimethylformamide is added 4.12 g of sodium hydride (56% in oil) and 27.7 g of 1-bromotetradecane. The mixture is heated on a steam bath until hydrogen evolution began and then chilled briefly to control the reaction. After the sodium hydride has reacted, the mixture is heated on a steam bath under nitrogen for 6 hours. The mixture is chilled, filtered and the solid washed with ethanol and with water to give ethyl 3-fluoro-4-(tetradecylamino)benzoate.

Workup

  1. temperaturechilled briefly
  2. customthe reaction
  3. temperaturethe mixture is heated on a steam bath under nitrogen for 6 hours
  4. temperatureThe mixture is chilled
  5. filtrationfiltered
  6. washthe solid washed with ethanol and with water

Sources & evidence

ORD record
ord-806a16932ef5428c82d709f074ea5b15
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

Loading…