p-Tolunitrile → HCID 178425648, compound

HRID 1274207Notes

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

Reactant 2

HCID 7724p-Tolunitrile

HCID 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

customis bubbled HCl for 1 hour
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-cbd5cbe176c14714822b8542721104be
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156776

Reaction notes

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