Butyraldehyde oxime → HCID 5273047, compound

HRID 1681926Notes

Reaction equation

HRID 1681926 reaction equation
[CH:1](=NO)CCC.C(=NO)CC.ClN1C(=O)CCC1=O.O1C=NC=N1.[CH3:25][C:26]1[CH:42]=[C:41]([C:43]2[N:47]=[C:46]([CH3:48])[O:45][N:44]=2)[CH:40]=[C:39]([CH3:49])[C:27]=1[O:28][CH2:29][CH2:30][CH2:31][C:32]1[O:36][N:35]=[C:34]([CH2:37][CH3:38])[CH:33]=1>N1C=CC=CC=1.C(OCC)(=O)C.CCCCCC.C(N(CC)CC)C.CN1CCCC1=O>[CH3:49][C:39]1[CH:40]=[C:41]([C:43]2[N:47]=[C:46]([CH3:48])[O:45][N:44]=2)[CH:42]=[C:26]([CH3:25])[C:27]=1[O:28][CH2:29][CH2:30][CH2:31][C:32]1[O:36][N:35]=[C:34]([CH2:37][CH2:38][CH3:1])[CH:33]=1

Participants

10

Reactant 5

HCID 8069Butyraldehyde oximeHCID 31398ChlorosuccinimideHCID 641641Propionaldehyde oximeHCID 5273046HCID 5273046, compoundHCID 64514631,2,4-Oxadiazole

Product 1

HCID 5273047HCID 5273047, compoundYield 58%

Reagents, catalysts & solvents 4

HCID 1049PyridineCatalystHCID 8471TriethylamineSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Following a procedure similar to that of Example 8(c) but substituting 2.6 g butyraldehyde oxime for the propionaldehyde oxime and using 3.99 g N-chlorosuccinimide, 2 drops pyridine, 50 ml N-methylpyrrolidinone, 2.7 g of the 1,2,4-oxadiazole of part (b) of Example 8 and 4.2 ml triethylamine, there was obtained after chromatography (MPLC, silica gel, 30:70 ethyl acetate/hexane) 2.06 g (58%) of the title compound as white needles, m.p. 69.0°-70.0° C. when recrystallized from methyl alcohol.

Sources & evidence

ORD record
ord-a9a521966d824293ad2194425002140a
Source dataset
uspto-grants-1992_12
Patent number
US05175178

Reaction notes

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