4-Fluorobenzoyl chloride → HCID 14664361, compound

HRID 1381907Notes

Reaction equation

HRID 1381907 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH3:2].[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>O1CCCC1>[CH2:17]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([F:19])=[CH:21][CH:22]=1)[CH3:18]

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 188985N-(1-Naphthyl)-N',N'-diethylethylenediamine

Product 1

HCID 14664361HCID 14664361, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8.0 g (33 mmol) of N,N-diethyl-N'-naphthalenyl-1,2-ethanediamine in 100 mL of tetrahydrofuran is treated with a solution of 6.8 g 4-fluorobenzoyl chloride in 50 mL of tetrahydrofuran and stirred at room temperature. After one hour, the solvent is evaporated on the rotary evaporator. The residue is dissolved in 200 mL of methylene chloride and washed with 200 mL of water and 4N sodium hydroxide to pH=14. The organic layer is dried over sodium sulfate, filtered and the solvent evaporated to provide the title compound.

Workup

  1. customthe solvent is evaporated on the rotary evaporator
  2. dissolutionThe residue is dissolved in 200 mL of methylene chloride
  3. washwashed with 200 mL of water and 4N sodium hydroxide to pH=14
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-e884890f96a647c9b34db8f534c3cf86
Source dataset
uspto-grants-1989_02
Patent number
US04804662

Reaction notes

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