1-Methylimidazole → HCID 13052622, compound

HRID 1081253Notes

Reaction equation

HRID 1081253 reaction equation
[P:1]([Cl:5])(Cl)([Cl:3])=[O:2].CN1C=CN=C1.[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1>>[P:1]([Cl:5])([Cl:3])(=[O:2])[O:20][C:17]1[CH:18]=[CH:19][C:14]([S:13][CH3:12])=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 13901-MethylimidazoleHCID 140864-(Methylthio)phenolHCID 24813Phosphorus oxychloride

Product 1

HCID 13052622HCID 13052622, compoundYield 42.8%

Procedure

To a solution of freshly distilled phosphoryl chloride (45 ml, 0.5 mol) and 1-methylimidazole (0.15 ml), is added 4-(methylthio)phenol (14, 0.1 mol) and the solution is heated under reflux for 20 h. The excess of phosphoryl chloride is removed by distillation and the residue distilled under reduced pressure to give the product (11 g, 42% yield); bp 135°-142° C. (2 mm Hg) 1H NMR (CDCl3) δ 2.39 (3H, S, SCH3), 7.22 (4 H, s, phenyl).

Workup

  1. temperaturethe solution is heated
  2. temperatureunder reflux for 20 h
  3. customThe excess of phosphoryl chloride is removed by distillation
  4. distillationthe residue distilled under reduced pressure

Sources & evidence

ORD record
ord-70a02711a40149d2b48167ab7c4b88eb
Source dataset
uspto-grants-1996_12
Patent number
US05585364

Reaction notes

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