Thionyl Chloride → HCID 23320952, compound

HRID 280662Notes

Reaction equation

HRID 280662 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:16]([Cl:17])=[CH:15][C:12]([CH2:13]O)=[CH:11][C:10]=2[Cl:18])=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:16]([Cl:17])=[CH:15][C:12]([CH2:13][Cl:21])=[CH:11][C:10]=2[Cl:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54111453HCID 54111453, compound

Product 1

HCID 23320952HCID 23320952, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst2×

Procedure

4-(4-Chlorophenylthio)-3,5-dichlorobenzyl alcohol (1.28 g, 4.00 mmol) was added to stirred thionyl chloride (5.0 ml) at ambient temperature. The solution was refluxed 15 minutes, treated with dimethylformamide (1 drop), refluxed 15 minutes, treated with more dimethylformamide (1 drop), and refluxed 1 hour. Thionyl chloride was evaporated under a stream of nitrogen, hexane (5 ml) was added and evaporated under a stream of nitrogen, and the residue was dried under vacuum. Hexane (10 ml) was added, the mixture was filtered through anhydrous magnesium sulfate, and the magnesium sulfate was washed well with hexane. The combined filtrate and washes were evaporated under vacuum and dried at 35° C. under vacuum to provide 1.35 g (100%) of 4-(4-chlorophenylthio)-3,5-dichlorobenzyl chloride. The chloride was suspended in absolute ethanol (10 ml) and stirred at ambient temperature while sodium azide (720 mg, 11.1 mmol) was added. The mixture was refluxed 3 hours, kept 16 hours at - 20° C., and evaporated to dryness under vacuum at 30° C. The residue was treated with diethyl ether (50 ml), filtered, and washed with diethyl ether. The combined filtrate and washes were evaporated under vacuum and dried to provide 1.38 g (100%) of 4-(4-chlorophenylthio)-3,5-dichlorobenzyl azide as a colorless viscous oil; 60 MHz 'H NMR (CDCl3) 4.35 s (2H), 7.03 dm (J=8.5 Hz, 2H), 7.23 dm (J=8.5 Hz, 2H), 7.38 s (2H); IR (neat): 2110 cm-1.

Workup

  1. temperatureThe solution was refluxed 15 minutes
  2. temperaturerefluxed 15 minutes
  3. temperaturerefluxed 1 hour
  4. customThionyl chloride was evaporated under a stream of nitrogen, hexane (5 ml)
  5. additionwas added
  6. customevaporated under a stream of nitrogen
  7. customthe residue was dried under vacuum
  8. additionHexane (10 ml) was added
  9. filtrationthe mixture was filtered through anhydrous magnesium sulfate
  10. washthe magnesium sulfate was washed well with hexane
  11. customThe combined filtrate and washes were evaporated under vacuum
  12. customdried at 35° C. under vacuum

Sources & evidence

ORD record
ord-ca8d760e98c4426f97e49e6ba39164ca
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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