Bromine → Pyrrolo(3,4-e)-1,4-diazepin-2(1H)-one, 3,7-dihydro-8-bromo-6,7-dimethyl-5-phenyl-

HRID 1074414Notes

Reaction equation

[CH3:1][C:2]1[N:3]([CH3:19])[CH:4]=[C:5]2[C:11]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[N:9][CH2:8][C:7](=[O:18])[NH:6]2.[Br:20]Br.C([O-])(O)=O.[Na+]>CO>[Br:20][C:4]1[N:3]([CH3:19])[C:2]([CH3:1])=[C:11]2[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:9][CH2:8][C:7](=[O:18])[NH:6][C:5]=12

Participants

Conditions

Temperature: -60 °C

Procedure

3,7-dihydro-6,7-dimethyl-5-phenylpyrrolo[3,4-e][1,4]diazepin-2(1H)-one (5.0 g, 0.020 mole) is dissolved in methanol (150 ml) and the obtained solution is cooled to -60° C. and stirred during the addition of a solution of bromine (3.4 g, 0.021 mole) in methanol (10 ml). After 20 minutes at -60° C., the reaction mixture is poured into an aqueous solution of NaHCO3 (1.5% w/v, 750 ml). The precipitate which forms is recovered by filtration and crystallized from methanol yielding 4.2 g of the compound of the title. M.p. 200°-2° C.

Workup

filtrationThe precipitate which forms is recovered by filtration
customcrystallized from methanol yielding 4.2 g of the compound of the title

Sources & evidence

ORD record: ord-1eff709048cc4cb1aab4f5696b5ac5f4
Source dataset: uspto-grants-1983_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04391817

Reaction notes

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