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Hydrochloric Acid → HCID 86200540, compound

HRID 718154
Notes
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Reaction equation

HRID 718154 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]#[N:6].[ClH:7].[CH2:8]([OH:10])[CH3:9]>>[ClH:7].[CH3:1][O:2][CH2:3][CH2:4][C:5](=[NH:6])[O:10][CH2:8][CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 61032Propanenitrile, 3-methoxy-

Product 1

HCID 86200540HCID 86200540, compoundYield 63%

Procedure

3-Methoxypropanenitrile (5.0 g, 58.8 mmol) was dissolved in anhydrous ethanol (50 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. The residue was slurried with hexanes (50 mL) and sonicated for 10 min. The solids were allowed to settle and the solvent was removed by decantation. This was repeated (3×). The solid was collected and dried under high vacuum for 5 h to afford ethyl 3-methoxypropanimidate hydrochloride (6.2 g, 63%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.03 (br s, 1H), 11.22 (br s, 1H), 4.42 (q, J=7.0 Hz, 2H), 3.60 (t, J=5.9 Hz, 2H), 3.23 (s, 3H), 2.87 (t, J=5.9 Hz, 2H), 1.33 (t, J=7.0 Hz, 3H).

Workup

  1. stirringstirred for 6 h
  2. customThe solvent was removed in vacuo
  3. customsonicated for 10 min
  4. customthe solvent was removed by decantation
  5. customThe solid was collected
  6. customdried under high vacuum for 5 h

Sources & evidence

ORD record
ord-087009a2667c42a281c7f3050fed48bb
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193719B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes