Water → 2-cyano-N-cyclopropylacetamide

HRID 279731Notes

Reaction equation

HRID 279731 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[C:5]([CH2:7][C:8](O)=[O:9])#[N:6].C(N=C=NC(C)C)(C)C.O>O1CCCC1.CC#N>[CH:1]1([NH:4][C:8](=[O:9])[CH2:7][C:5]#[N:6])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 9740Cyanoacetic acidHCID 12734DiisopropylcarbodiimideHCID 69828Cyclopropylamine

Product 1

HCID 21678842-cyano-N-cyclopropylacetamideYield 84.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

Cyclopropylamine (5.0 grams, 88 mmole) was combined with 7.5 grams (g) (88 mmol) of cyanoacetic acid in 50 milliliters (ml) tetrahydrofuran (THF) and 50 ml CH3CN. Diisopropylcarbodiimide (20 g, 97 mmol) dissolved in 10 ml THF was added dropwise. The reaction mixture exothermed and a white precipitate formed. The mixture was stirred at 20° C. for 20 hours, 5 ml water was added and the reaction mixture was stirred another 5 minutes. The precipitate was filtered off and the filtrate evaporated giving a white solid which was then recrystallized to yield 9.2 g (74 mmol) of N-(cyclopropyl)-2-cyanoacetamide, a white solid (m.p. 104°-106° C.) (84% yield).

Workup

  1. additionwas added dropwise
  2. customa white precipitate formed
  3. stirringthe reaction mixture was stirred another 5 minutes
  4. filtrationThe precipitate was filtered off
  5. customthe filtrate evaporated
  6. customgiving a white solid which
  7. customwas then recrystallized

Sources & evidence

ORD record
ord-88e8655de7aa40379f5b7919c56a9195
Source dataset
uspto-grants-1986_05
Patent number
US04586954

Reaction notes

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