p-Tolunitrile → HCID 178425648, compound

HRID 651391Notes

Reaction equation

HRID 651391 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%). 1H NMR (CDCl3): δ 2.44 (s, 3H), 4.52 (s, 3H), 7.36 (d, 2H), 8.29 (d, 2H).

Workup

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

Sources & evidence

ORD record
ord-976f0249f55649afae6a7a761e8c4686
Source dataset
uspto-grants-2001_08
Patent number
US06281217B1

Reaction notes

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