Hydrochloric Acid → Propanimidic acid, 2,2-dimethyl-, ethyl ester, hydrochloride

HRID 718148Notes

Reaction equation

HRID 718148 reaction equation
[C:1](#[N:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[ClH:7].[CH2:8]([OH:10])[CH3:9]>>[ClH:7].[C:1](=[NH:6])([O:10][CH2:8][CH3:9])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 12416Pivalonitrile

Product 1

HCID 12235056Propanimidic acid, 2,2-dimethyl-, ethyl ester, hydrochlorideYield 100%

Procedure

Pivalonitrile (1.3 mL, 12.0 mmol) was dissolved in anhydrous ethanol (28 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 54 h. The solvent was removed in vacuo to afford ethyl pivalimidate hydrochloride (2.0 g, 100%) as an off white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.19 (br s, 1H), 4.42 (q, J=6.9 Hz, 2H), 1.33 (t, J=6.8 Hz, 3H), 1.24 (s, 9H).

Workup

  1. stirringstirred for 54 h
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-521f7355abe84c12ae624f4b2752ecf8
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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