Benzoyl chloride → HCID 54431880, compound

HRID 235124Notes

Reaction equation

HRID 235124 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[C:22]2[N:25]2[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]2)=[CH:17][CH:16]=1>CC(C)=O>[C:5]([NH:3][C:2]([NH:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[C:22]2[N:25]2[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]2)=[CH:17][CH:16]=1)=[S:1])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 54431880HCID 54431880, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

To a mixture of ammonium thiocyanate (0.376 g, 4.94 mmol) in acetone (5 mL) was added benzoyl chloride (0.57 mL, 4.94 mmol) dropwise. The mixture (white precipitate) was refluxed 45 minutes which resulted in a yellow heterogeneous solution. A solution of 7-Amino-1-(4-methyl-1-piperazinyl)-naphthalene (1.0 g, 4.14 mmol) in acetone (25 mL) was added dropwise (10 mL acetone rinse also added). The mixture was refluxed 4 hours and allowed to stir overnight at ambient temperature. The mixture was concentrated onto silica gel and flash chromatographed (2×3.5 inches). Gradient elution with ethyl acetate/hexane of from 50% to 100% gave an unweighed forerun. Continued gradient elution with 10 to 40% ethanol/ethyl acetate gave 1.3 g (77%) of title product as a yellow foam which was suitable for use without further purification. The compound was found to slowly decompose at room temperature. A sample recrystallized from ethyl acetate/methylene chloride for analysis: mp 160°-250° C. 1H NMR (DMSOd6, D2O) δ 8.74 (s, 1H), 7.97 (d, J=7.5 Hz, 1H), 7.91 (d, J=9 Hz, 1H), 7.70-7.51 (m, 5H), 7.42 (t, J=8 Hz, 1H), 7.12 (d, J=7 Hz, 1H), 3.11 (m, 4 H), 2.79 (br s, 4H), 2.39 (s, 3H). HRMS m/e calculated for C23H24N4OS: 404.1661. Observed m/e: 404.1633.

Workup

  1. temperatureThe mixture (white precipitate) was refluxed 45 minutes which
  2. customresulted in a yellow heterogeneous solution
  3. washrinse also
  4. additionadded)
  5. temperatureThe mixture was refluxed 4 hours
  6. concentrationThe mixture was concentrated onto silica gel and flash
  7. customchromatographed (2×3.5 inches)
  8. washGradient elution with ethyl acetate/hexane of from 50% to 100%
  9. customgave an unweighed forerun
  10. washelution with 10 to 40% ethanol/ethyl acetate

Sources & evidence

ORD record
ord-d1f23cafb6b345de93b16fb72907c377
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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