Hydrochloric Acid → Ethyl 2-methylpropanimidate--hydrogen chloride (1/1)

HRID 718150Notes

Reaction equation

HRID 718150 reaction equation
[C:1](#[N:5])[CH:2]([CH3:4])[CH3:3].[ClH:6].[CH2:7]([OH:9])[CH3:8]>>[ClH:6].[C:1](=[NH:5])([O:9][CH2:7][CH3:8])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6559Isobutyronitrile

Product 1

HCID 12816252Ethyl 2-methylpropanimidate--hydrogen chloride (1/1)Yield 82%

Procedure

Isobutyronitrile (1 g, 14.5 mmol) was dissolved in anhydrous ethanol (30 mL) under an atmosphere of Ar. The solution was cooled to 0° C., saturated with HCl gas, stirred for 6 h, allowed to warm to RT, and stirred for 6 h. The solvent was removed in vacuo to afford ethyl isobutyrimidate hydrochloride (1.8 g, 82%) as a colorless solid. 1H NMR (400 MHz, DMSO-d6): δ 11.78 (br s, 1H), 11.05 (br s, 1H), 4.40 (q, J=7.0 Hz, 2H), 2.93-2.92 (m, 1H), 1.33 (t, J=7.0 Hz, 3H), 1.16 (d, J=6.9 Hz, 6H).

Workup

  1. stirringstirred for 6 h
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b848dd8932684118b5196eeb2c474870
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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