Methylamine → HCID 22901847, compound

HRID 1489504Notes

Reaction equation

HRID 1489504 reaction equation
[CH3:1][NH2:2].[O:3]=[C:4]1[N:8]([CH2:9][C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=O)[N:7]=C(C(F)(F)F)O1>C(#N)C>[NH2:7][N:8]1[CH:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:2]([CH3:1])[C:4]1=[O:3]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22901841HCID 22901841, compound

Product 1

HCID 22901847HCID 22901847, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

75 ml of aqueous methylamine solution (40%) are added to a solution of 12.6 g of 2,3-dihydro-2-oxo-3-tert-butylcarbonylmethyl-5-trifluoromethyl-1,3,4-oxadiazole in 50 ml of acetonitrile. After the slightly exothermal reaction has subsided, the reaction mixture is stirred for 2 hours at room temperature and then for 14 hours at 80° and then evaporated the liquid residue is treated with ice-water, and the aqueous mixture is extracted three times by shaking with ethyl acetate. The combined ethyl acetate phases are dried and evaporated, and the oily orange residue is recrystallized from hexane. This gives the title compound in the form of pale yellow crystals which melt at 100°-105°.

Workup

  1. customAfter the slightly exothermal reaction
  2. waitfor 14 hours at 80°
  3. customevaporated the liquid residue
  4. additionis treated with ice-water
  5. extractionthe aqueous mixture is extracted three times
  6. stirringby shaking with ethyl acetate
  7. dry with materialThe combined ethyl acetate phases are dried
  8. customevaporated
  9. customthe oily orange residue is recrystallized from hexane

Sources & evidence

ORD record
ord-8bb9ce9ce7d341509fa44d8a1073ac34
Source dataset
uspto-grants-1997_10
Patent number
US05679623

Reaction notes

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