Ammonia → HCID 21069923, compound

HRID 1726542Notes

Reaction equation

HRID 1726542 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH:5]([O:8][CH2:9][CH2:10][O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:6]#[N:7].[NH3:16]>CO>[CH3:1][S:2][CH2:3][CH2:4][CH:5]([O:8][CH2:9][CH2:10][O:11][Si:12]([CH3:13])([CH3:15])[CH3:14])[C:6]([NH2:16])=[NH:7]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21069924HCID 21069924, compound

Product 1

HCID 21069923HCID 21069923, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

A solution of intermediate 18, 4-(methylthio)-2-(2-(trimethylsilyloxy)ethoxy)butanenitrile, (4.9 g, 0.02 mol) in 30 mL of methanol was saturated with ammonia. The flask was then sealed and heated in an oil bath at 80-90° C. for 16 hrs. After cooling, the flask was opened and the mixture concentrated in vacuo to give the title compound in essentially quantitative yield as a very viscous oil. 1H NMR (300 MHz, CDCl3) δ ppm:3.94-4.02 (1H, m) 3.76-3.94 (3H, m) 3.68-3.77 (2H, m) 3.52-3.62 (2H, m) 2.53-2.67 (2H, m) 2.07 (3H, s) 1.89-2.01 (2H, m); LC/MS193 (M+H).

Workup

  1. customThe flask was then sealed
  2. temperatureAfter cooling
  3. concentrationthe mixture concentrated in vacuo

Sources & evidence

ORD record
ord-26267a69109e4c519b146e52e94392c4
Source dataset
uspto-grants-2009_02
Patent number
US07491819B1

Reaction notes

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