1-Chloropropane → HCID 21041471, compound

HRID 1698487Notes

Reaction equation

HRID 1698487 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[S-2].[Na+].[Na+].Cl[CH2:14][CH2:15][CH3:16].O[O:18][S:19]([O-])=[O:20].[K+]>CN(C)C=O>[CH2:14]([S:19]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)(=[O:20])=[O:18])[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 108991-ChloropropaneHCID 121634-ChlorobenzonitrileHCID 14804Sodium SulfideHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 21041471HCID 21041471, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To 4-chlorobenzonitrile (5 g) in dry N,N-dimethylformamide (50 mL), under nitrogen, was added sodium sulphide (3.11 g), and the stirred mixture heated in an oil bath at 130° C. for 48 h. The mixture was cooled to room temperature, 1-chloropropane (4.0 mL) added and stirring continued for 12 h. The mixture was cooled in an ice-water bath and “OXONE” (34 g) added with stirring. The water bath was removed after 2 h, and the mixture stirred at room temperature for 14 h. The reaction mixture was then diluted with an equal volume of ethyl acetate, solids removed by filtration, and solvent stripped at reduced pressure. The residue was chromatographed on silica gel, eluent 15 to 30% ethyl acetate in isohexane, and the title compound crystallised from isohexane as a white solid. 1H NMR (360 MHz, CDCl3) δ 8.05 (2H, d, J=8.1 Hz), 7.88 (2H, d, J=8.3 Hz), 3.10 (2H, m), 1.76 (2H, m), 1.02 (3H, t, J=7.4 Hz).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. temperatureThe mixture was cooled in an ice-water bath
  3. stirringwith stirring
  4. customThe water bath was removed after 2 h
  5. stirringthe mixture stirred at room temperature for 14 h
  6. additionThe reaction mixture was then diluted with an equal volume of ethyl acetate, solids
  7. customremoved by filtration, and solvent
  8. customThe residue was chromatographed on silica gel, eluent 15 to 30% ethyl acetate in isohexane
  9. customthe title compound crystallised from isohexane as a white solid

Sources & evidence

ORD record
ord-f6d57e288445427f899c77c70f000923
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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