N'-Hydroxycyclopropanecarboximidamide synthesis
- Product Name:N'-Hydroxycyclopropanecarboximidamide
- CAS Number:51285-13-3
- Molecular formula:C4H8N2O
- Molecular Weight:100.12
5500-21-0
51285-13-3
General procedure for the synthesis of N-hydroxycyclopropanecarboxamidine from cyclopropanecarbonitrile: A mixture of cyclopropanecarbonitrile (5 g, 74.6 mmol) and hydroxylamine (50 wt% aqueous, 5.91 g, 89.5 mmol) in ethanol (15 mL) was reacted with stirring at 80 °C overnight. Upon completion of the reaction, the mixture was cooled to room temperature and the volatile solvent was subsequently removed under reduced pressure to afford the crude product N-hydroxycyclopropanecarboxamidine (7.0 g, 94% yield). The product could be directly used in the subsequent reaction without further purification. The product was analyzed by LCMS showing m/z = 101.2 [M + H]+, which was consistent with the theoretically calculated value (exact mass of C4H8N2O: 100.1).1H NMR (400 MHz, DMSO-d6) data were as follows: δ 0.54-0.60 (m, 2H), 0.61-0.66 (m, 2H), 1.28-1.36 (m, 1H) , 5.18 (bs, 2H), 8.68 (bs, 1H).
5500-21-0
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51285-13-3
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$12.00/100mg
Yield:51285-13-3 80%
Reaction Conditions:
with hydroxylamine;potassium carbonate in ethanol;water at 20; for 18 h;
Steps:
N-hydroxy-cyclopropanecarboxamidine
6.00 g (43.41 mmol) potassium carbonate are dissolved in 19 ml of water, 60 ml of ethanol, 3.00 g (43.17 mmol) hydroxylamine and 3.25 ml (43.25 mmol) cyclopropylcyamide are added. The reaction mixture is stirred for 18 hours at ambient temperature, then evaporated down and re-evaporated with toluene. The residue is mixed with ethanol, suction filtered and the filtrate is evaporated to dryness. Yield: 3.47 g (80% of theoretical)
References:
US2007/238730,2007,A1 Location in patent:Page/Page column 24