Hydrazine hydrate (1:1) → N-[6-(benzyloxymethyl)-3-oxo-2,5-dihydro-1,2,4-triazin-4-yl]acetamide

HRID 570907Notes

Reaction equation

[CH2:1]([O:8][CH2:9][C:10](=O)[CH2:11][N:12]1[N:16]=[C:15]([CH3:17])[O:14][C:13]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:21][NH2:22]>C(O)(C)C>[CH2:1]([O:8][CH2:9][C:10]1[CH2:11][N:12]([NH:16][C:15](=[O:14])[CH3:17])[C:13](=[O:18])[NH:21][N:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 3-(3-benzyloxy-2-oxo-propyl)-5-methyl-1,3,4-oxadiazol-2-one (36.4 g, 139 mmol) in isopropanol (140 mL) was added hydrazine hydrate (62 wt % in water, 11.8 mL, 152 mmol) in at room temperature in one portion. The mixture was heated to 75° C. for 24 h. The volatiles were removed under reduced pressure, and the remaining brown oil was purified by flash chromatography (7% MeOH/dichloromethane) to furnish the desired product as a yellowish solid. 1H NMR (400 MHz, CDCl3) 2.04 (s, 3H), 4.12 (s, 2H), 4.23 (s, 2H), 4.54 (s, 2H), 7.24-7.44 (m, 5H), 8.25 (s, 1H), 8.69 (s, 1H).

Workup

customThe volatiles were removed under reduced pressure
customthe remaining brown oil was purified by flash chromatography (7% MeOH/dichloromethane)

Sources & evidence

ORD record: ord-07054306b4934c98bec0d0b8802086a8
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024019B2

Reaction notes

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