Diethyl Ether → HCID 70531060, compound

HRID 2166832Notes

Reaction equation

HRID 2166832 reaction equation
O[CH:2]([N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[Cl:11].S(Cl)([Cl:19])=O.CCOCC>C(Cl)(Cl)Cl>[ClH:10].[Cl:19][CH:2]([N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[Cl:11]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 20497976HCID 20497976, compound

Product 1

HCID 70531060HCID 70531060, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1-(α-Hydroxy-2,4-dichlorophenethyl)imidazole, 12.85 g (0.05 mole), was dissolved in 100 ml chloroform and 8.33 g (0.07 mole) thionyl chloride was added to cause immediate formation of a solid precipitate. The mixture was refluxed three hours causing total solution of all solids. No precipitate formed on cooling to ambient temperature. A solid precipitate formed on pouring the chloroform solution into 500 ml of ether. The solid was collected and dried, 8.67 g (55.6%), m.p. 165°-167° C. Both ir and H1 nmr spectra supported the chemical structure. DMSO δ TMS 7.4 (m, 6H, aryl/imidazole); 5.78 (t, 1H, CH); 4.1 (d,2H, CH2).

Workup

  1. temperatureThe mixture was refluxed three hours
  2. customNo precipitate formed
  3. customA solid precipitate formed
  4. customThe solid was collected
  5. customdried

Sources & evidence

ORD record
ord-c81e648682e947eeb795374a148a2a1f
Source dataset
uspto-grants-1983_06
Patent number
US04389409

Reaction notes

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