Benzylethanolamine → HCID 18798226, compound

HRID 1003723Notes

Reaction equation

HRID 1003723 reaction equation
[C:1]1([C:7]([CH:9]=[O:10])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([NH:18][CH2:19][CH2:20]O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([N:18]1[CH2:19][CH2:20][O:10][CH:9]1[C:7](=[O:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 4348BenzylethanolamineHCID 14090Phenylglyoxal

Product 1

HCID 18798226HCID 18798226, compoundYield 90%

Procedure

Agami et al, Tetrahedron Lett., (1993) 34, 7061 describes the reaction of phenylglyoxal with (R)-N-methylphenylglycinol in refluxing acetonitrile to give (5R)-3,5-diphenyl-4-methyl-1,4-oxazin-2-one. Under the same conditions, however, we have found that the reaction of phenylglyoxal with N-benzylethanolamine gives predominantly (>90%) N-benzyl-2-benzoyloxazolidine. The desired product, N-benzyl-3-phenyl-1,4-oxazin-2-one was formed at a low level (5%).

Sources & evidence

ORD record
ord-7746a0164a4942df949b6000a2817ce9
Source dataset
uspto-grants-2000_04
Patent number
US06046325

Reaction notes

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