Morpholine → HCID 66844501, compound

HRID 2095204Notes

Reaction equation

HRID 2095204 reaction equation
[C:1]([C:3](=[C:7]([S:10][CH3:11])SC)C(O)=O)#[N:2].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(N(CC)CC)C>CO>[CH3:11][S:10][C:7]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[CH:3][C:1]#[N:2]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 5325463HCID 5325463, compound

Product 1

HCID 66844501HCID 66844501, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

2-Cyano-3,3-bis-methylsulfanyl-acrylic acid (the compound of formula (F), 35 g, 0.18 mol) was dissolved in 250 mL of methanol. Morpholine (the compound of formula (O), 28 mL, 0.32 mol) and triethylamine (25 mL, 0.18 mol) were added to the solution while the temperature was maintained at approximately 20° C. The reaction was warmed slightly to a temperature of between 25-27° C. and this temperature was maintained overnight. The solvents were then removed under reduced pressure taking care not to heat the reaction mixture. The resulting crude material was filtered through a short silica gel column eluting with MeOH:CH2Cl2=1:5 to afford the 3-methylsulfanyl-3-morpholin-4-yl-acrylonitrile of formula (P).

Workup

  1. temperatureThe reaction was warmed slightly to a temperature of between 25-27° C.
  2. temperaturethis temperature was maintained overnight
  3. customThe solvents were then removed under reduced pressure
  4. temperatureto heat the reaction mixture
  5. filtrationThe resulting crude material was filtered through a short silica gel column
  6. washeluting with MeOH

Sources & evidence

ORD record
ord-e3fef307526b4862a8f0638ec594cdfb
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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