Hydroxylamine → HCID 86685713, compound

HRID 1055274Notes

Reaction equation

[O:1]=[C:2]1[NH:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=O.[NH2:18][OH:19]>CCO.O>[O:1]=[C:2]1[NH:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[N:18][OH:19]

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 2-[2-(2-oxoimidazolidin-1-yl)ethoxy]benzaldehyde (10.0 g, 0.043 mol) in EtOH (100 mL) is heated to 50° C. At this temperature, a hydroxylamine solution (4.5 g, 0.068 mol, 50% in water, Aldrich) in EtOH (10 mL) is added. The reaction medium is then stirred for 6 hours at a temperature between 50° C. and 70° C. The reaction medium is evaporated under reduced pressure (Tbath 45° C., 65-70 mbar) until a suspension is obtained. The crude reaction product is then taken up in water (5 mL). The solution obtained is cooled to 5° C. and maintained at this temperature for 15 hours. The precipitate obtained is filtered and washed on the filter with an EtOH/water mixture (2 mL/2 mL) and then with an EtOH/petroleum ether mixture (1 mL/4 mL) and then with petroleum ether (2*10 mL). The solid is then dried under atmospheric pressure at room temperature.

Workup

customThe reaction medium is evaporated under reduced pressure (Tbath 45° C., 65-70 mbar) until a suspension
customis obtained
customThe crude reaction product
customThe solution obtained
temperaturemaintained at this temperature for 15 hours
customThe precipitate obtained
filtrationis filtered
washwashed on the
filtrationfilter with an EtOH/water mixture (2 mL/2 mL)
customThe solid is then dried under atmospheric pressure at room temperature

Sources & evidence

ORD record: ord-5c017ce6543d479bbc42f20ebc7be88a
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394380B2

Reaction notes

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