Hydroxylamine → HCID 178450469, compound

HRID 1664202Notes

Reaction equation

HRID 1664202 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][CH2:5][C:6]([CH3:10])([CH3:9])[C:7]#[N:8].[NH2:11][OH:12]>CCO>[Cl:1][CH2:2][CH2:3][O:4][CH2:5][C:6]([CH3:10])([CH3:9])[C:7]([NH:11][OH:12])=[NH:8]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 553031313-(2-Chloroethoxy)-2,2-dimethylpropanenitrile

Product 1

HCID 178450469HCID 178450469, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
77.5 °C

Procedure

3-(2-Chloroethoxy)-2,2-dimethylpropanenitrile (6.1 g, 37.7 mmol) was placed together with 50% aqueous hydroxylamine (3.1 g, 37.7 mmol) in 60 mL EtOH and warmed at 75-80° C. with stirring for 18 h. The solution was concentrated and then azeotroped with EtOH to provide (9.4 g, ˜80% pure) of the title compound as a gum. 1H NMR (300 MHz, CDCl3) δ: 1.17 (s, 6H), 3.40 (s, 2H), 3.58-3.73 (m, 4H), 5.16 (s, 2H). LC/MS (M+H): 195.

Workup

  1. concentrationThe solution was concentrated
  2. customazeotroped with EtOH

Sources & evidence

ORD record
ord-1dbcdd2d67d547a693af5520e520b44b
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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