Ammonium Chloride → Benzyl (2-amino-2-iminoethyl)carbamate hydrochloride

HRID 588707Notes

Reaction equation

HRID 588707 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)#[N:2].C[O-].[Na+].[Cl-:18].[NH4+:19]>CO>[ClH:18].[NH2:2][C:1](=[NH:19])[CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 244143Benzyl CyanomethylcarbamateHCID 10942334Sodium Methoxide

Product 1

HCID 18943499Benzyl (2-amino-2-iminoethyl)carbamate hydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzyl cyanomethylcarbamate (65.4 g, 344 mmol) in methanol was added sodium methoxide (7.86 mL, 34.4 mmol, 25% in methanol). The mixture was stirred at ambient temperature for 24 h. Ammonium chloride (18.4 g, 344 mmol) was then added. The mixture was stirred at ambient temperature for another 24 h, and concentrated under reduced pressure. The resulting material was added into hexane/ethyl acetate (1:1) (240 mL) and ether (50 mL), stirred at ambient temperature for 1.5 h, then filtered to provide the title compound as a pale colored solid (78.8 g, 94% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.79 (br. s., 4H), 7.78 (t, J=5.5 Hz, 1H), 7.24-7.47 (m, 5H), 5.07 (s, 2H), 3.98 (d, J=5.5 Hz, 2H). MS m/z 208.2 (M+1), retention time=0.64 min.

Workup

  1. stirringThe mixture was stirred at ambient temperature for another 24 h
  2. concentrationconcentrated under reduced pressure
  3. additionThe resulting material was added into hexane/ethyl acetate (1:1) (240 mL) and ether (50 mL)
  4. stirringstirred at ambient temperature for 1.5 h
  5. filtrationfiltered

Sources & evidence

ORD record
ord-f31ae44ffef242ffb286f63b1e078c15
Source dataset
uspto-grants-2016_01
Patent number
US09227982B2

Reaction notes

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