p-Tolunitrile → HCID 178425648, compound

HRID 650999Notes

Reaction equation

HRID 650999 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[N:8])=[CH:3][CH:2]=1.C(Cl)(Cl)[Cl:11].C[OH:15]>>[ClH:11].[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([C:7](=[NH:8])[OH:15])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 7724p-TolunitrileHCID 21584188Chloroform methanol

Product 1

HCID 178425648HCID 178425648, compoundYield 99%

Conditions

Temperature
10 °C

Procedure

To a solution of p-tolunitrile (10.1 g, 86.21 mmol) in 100 ml CHCl3:MeOH (1:1) cooled to 5° C. in an ice-water bath is bubbled HCl for 1 hour to reach saturation. The solution is stirred at 10° C. for 43 hours, then concentrated under reduced pressure to yield p-methylbenzimidate hydrochloride as pale yellow crystals (15.98 g, 99%).

Workup

  1. customis bubbled HCl for 1 hour
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-49d0955c29b04559b47cf8230e150048
Source dataset
uspto-grants-2001_08
Patent number
US06277873B1

Reaction notes

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