Dimethyl Sulfoxide → 6,7-Dichloro-2-methyl-10-(4-methyl-piperazin-1-yl)-2,4-dihydro-1,2,3,4,9-pentaaza-benzo[f]azulene

HRID 2412399Notes

Reaction equation

Cl.[NH2:2][C:3]1[C:4]2[C:5](=[N:16][N:17]([CH3:19])[N:18]=2)[NH:6][C:7]2[CH:13]=[C:12]([Cl:14])[C:11]([Cl:15])=[CH:10][C:8]=2[N:9]=1.CS(C)=O.[CH3:24][N:25]1[CH2:30][CH2:29]N[CH2:27][CH2:26]1>C1(C)C=CC=CC=1>[Cl:14][C:12]1[C:11]([Cl:15])=[CH:10][C:8]2[N:9]=[C:3]([N:2]3[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]3)[C:4]3[C:5](=[N:16][N:17]([CH3:19])[N:18]=3)[NH:6][C:7]=2[CH:13]=1

Participants

Conditions

Temperature: 125 °C

Procedure

10-Amino-6,7-dichloro-2-methyl-2,4-dihydro-1,2,3-triazolo[4,5-b][1,5]benzodiazepine hydrochloride (0.84 g) was added to a mixture of dry dimethylsulphoxide (5 ml), toluene (5 ml) and N-methylpiperazine (1 ml), which had been purged with nitrogen for 20 minutes. The stirred solution was then heated at 125° C. (oil bath) under nitrogen for 16 hours, cooled to room temperature, and distilled water (10 ml) added, keeping the temperature below 25° C. After stirring at 5° C. for half an hour, the suspension obtained was filtered off and dried at 70° C. under reduced pressure to leave a yellow-brown solid which was recrystallised from ethyl acetate/n-hexane to give a yellow crystalline solid, melting point 217.5°-218.5° C.

Workup

customhad been purged with nitrogen for 20 minutes
temperaturecooled to room temperature
distillationdistilled water (10 ml)
additionadded
customthe temperature below 25° C
customthe suspension obtained
filtrationwas filtered off
customdried at 70° C. under reduced pressure
customto leave a yellow-brown solid which
customwas recrystallised from ethyl acetate/n-hexane
customto give a yellow crystalline solid, melting point 217.5°-218.5° C.

Sources & evidence

ORD record: ord-6979540377ab44c2b7d5de891507c377
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04492699

Reaction notes

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