Methyl Chloride → 1-Methyl-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

HRID 1414514Notes

Reaction equation

HRID 1414514 reaction equation
[C:1]1([N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][C:10](=[O:18])[CH2:9][C:8]2=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCl.[CH2:22]([O-])C.[Na+]>>[C:1]1([N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH3:22])[C:10](=[O:18])[CH2:9][C:8]2=[O:19])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6327Methyl ChlorideHCID 2723922Sodium ethoxideHCID 10824683N-Desmethyl Dechloro Clobazam

Product 1

HCID 146976571-Methyl-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Procedure

Starting from 1-phenyl 1,2,4,5-tetrahydro 2,4-dioxo 3H-1,5benzodiazepine, obtained in the example VIII, by acting methyl chloride in the presence of sodium ethanolate, there is obtained 1-phenyl 5-methyl 1,2,4,5-tetrahydro 2,4-dioxo 3H-1,5-benzodiazepine, melting at 144°-146° C after recrystallisation in isopropanol. Analysis: C16H14N2O2Calculated: C % 72.16; H % 5.30; N % 10.52; Found: 72.31; 5.51; 10.51.

Workup

  1. customobtained in the example VIII

Sources & evidence

ORD record
ord-d75f218a1c21441789747ef80c301892
Source dataset
uspto-grants-1977_01
Patent number
US04001408

Reaction notes

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