Hydrochloric Acid → Ethyl 3-hydroxymethyl-5-methoxymethyl-benzimidate hydrochloride

HRID 1167339Notes

Reaction equation

HRID 1167339 reaction equation
[ClH:1].[OH:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH2:12][O:13][CH3:14])[CH:11]=1)[C:7]#[N:8].[CH2:15]([OH:17])[CH3:16]>>[ClH:1].[OH:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH2:12][O:13][CH3:14])[CH:11]=1)[C:7](=[NH:8])[O:17][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 229962313-Hydroxymethyl-5-methoxymethyl-benzonitrile

Product 1

HCID 22996175Ethyl 3-hydroxymethyl-5-methoxymethyl-benzimidate hydrochlorideYield 100%

Procedure

Hydrogen chloride gas was passed through a solution of 3-hydroxymethyl-5-methoxymethyl-benzonitrile (720 mg, 4.063 mmol) in anhydrous ethanol (25 mL) at 0° C. After 1 h, hydrogen chloride gas was stopped and the reaction vessel was sealed with a septum. After stirring at room temperature for 1 d, the reaction vessel was cooled to 0° C. and the septum was removed. The solvent was evaporated in vacuo to afford ethyl 3-hydroxymethyl-5-methoxymethyl-benzimidate hydrochloride as a white solid (1.05 g, 100%).

Workup

  1. customthe reaction vessel was sealed with a septum
  2. temperaturethe reaction vessel was cooled to 0° C.
  3. customthe septum was removed
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-e3998efe2a4b4708813cb518abdb9c15
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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