1-Bromopropane → 1-phenyl 5-propyl 8-chloro 1,2,4,5-tetrahydro 2,4-dioxo 3H-1,5-benzodiazepine

HRID 1414517Notes

Reaction equation

[CH2:1](Br)[CH2:2][CH3:3].[I-].CC[O-].[Na+].[C:10]1([N:16]2[C:22]3[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=3[NH:20][C:19](=[O:28])[CH2:18][C:17]2=[O:29])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([N:16]2[C:22]3[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=3[N:20]([CH2:1][CH2:2][CH3:3])[C:19](=[O:28])[CH2:18][C:17]2=[O:29])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 4

HCID 78401-Bromopropane

HCID 30165Iodide Ion

HCID 89657Desmethylclobazam

HCID 2723922Sodium ethoxide

Product 1

HCID 214876941-phenyl 5-propyl 8-chloro 1,2,4,5-tetrahydro 2,4-dioxo 3H-1,5-benzodiazepine

Procedure

In the same manner by acting propyl bromide or iodide in the presence of sodium ethylate, starting from 1-phenyl 8-chloro 1,2,4,5-tetrahydro 2,4-dioxo 3H-1,5-benzodiazepine, there is obtained 1-phenyl 5-propyl 8-chloro 1,2,4,5-tetrahydro 2,4-dioxo 3H-1,5-benzodiazepine (R1 = H, R2 = Cl, R3 =C3H7, R4 = C6H5) melting at 192°-194° C upon recrystallisation in ethanol. Analysis: c18H17ClN2O2 ; Calculated: C % 65.75; H % 5.21; N % 8.52; Found : 65.66; 5.17; 8.60.

Sources & evidence

ORD record: ord-f1f8565d233a4ac89f768191a21afab8
Source dataset: uspto-grants-1977_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04001408

Reaction notes

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