Sodium Methoxide → N-benzoyl-3-methoxycaprolactam

HRID 1682379Notes

Reaction equation

HRID 1682379 reaction equation
ClC1CCCNC(=O)C1.C[O-].[Na+].[C:13]([N:21]1[CH2:26][CH2:25]O[CH2:23][C:22]1=[O:27])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:28][O:29][CH:30]1[CH2:37][CH2:36][CH2:35][NH:34][C:32](=[O:33])[CH2:31]1>>[CH3:28][O:29][CH:30]1[CH2:37][CH2:36][CH2:35][NH:34][C:32](=[O:33])[CH2:31]1.[C:13]([N:21]1[CH2:26][CH2:25][CH2:31][CH:30]([O:29][CH3:28])[CH2:23][C:22]1=[O:27])(=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 10942334Sodium MethoxideHCID 122940964-Benzoylmorpholin-3-oneHCID 190438224-Methoxyazepan-2-oneHCID 193693183-Chlorocaprolactam

Product 2

HCID 19043821N-benzoyl-3-methoxycaprolactamHCID 190438224-Methoxyazepan-2-one

Procedure

3-Methoxycaprolactam was prepared from 3-chlorocaprolactam (prepared as described in Francis, et al. J. Am. Chem. Soc. 1958, 80, 6238) and sodium methoxide according to the method of Kondelikova, et al. (Collect. Czech. Chem. Commun. 1971, 36(9), 3391). The desired product N-benzoyl-3-methoxycaprolactam is synthesized as for N-benzoyl-3-oxomorpholine (Example I) using 3 -methoxycaprolactam in place of morpholin-3-one.

Sources & evidence

ORD record
ord-9aa69dbbb2814954beb15485a083d590
Source dataset
uspto-grants-1997_06
Patent number
US05635103

Reaction notes

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