Propionyl chloride → HCID 22135221, compound

HRID 1826703Notes

Reaction equation

[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[C:6]([C:8]1([CH3:32])[CH2:14][C:13]2[CH:15]=[C:16]3[O:21][CH2:20][O:19][C:17]3=[CH:18][C:12]=2[C:11]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[C:24]([CH3:31])[CH:23]=2)=[N:10][NH:9]1)#[N:7]>>[C:6]([C:8]1([CH3:32])[CH2:14][C:13]2[CH:15]=[C:16]3[O:21][CH2:20][O:19][C:17]3=[CH:18][C:12]=2[C:11]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[C:24]([CH3:31])[CH:23]=2)=[N:10][N:9]1[C:1](=[O:4])[CH2:2][CH3:3])#[N:7]

Participants

Reactant 2

HCID 62324Propionyl chloride

HCID 22135224HCID 22135224, compound

Product 1

HCID 22135221HCID 22135221, compoundYield 77%

Conditions

Temperature: 25 °C

Procedure

To 55 ml of propionyl chloride 7.06 g (19.4 millimoles) of (±)-8-cyano-7,8-dihydro-8-methyl-5-(3-methyl-4-nitro-phenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine are added at 15° C. The reaction mixture is stirred at 25° C. for 8 days and evaporated in vacuo. To the residue 200 ml of water are added. The mixture is stirred under cooling with icecold water for an hour. The precipitated crystals are filtered and washed with icecold water. The crude product obtained is recrystallized from 100 ml of acetonitrile. The crystals are filtered, washed with acetonitrile and ether and dried. Thus 6.30 g of the desired compound are obtained, yield 77%, mp.: 191–193° C.

Workup

customevaporated in vacuo
additionTo the residue 200 ml of water are added
stirringThe mixture is stirred
temperatureunder cooling with icecold water for an hour
filtrationThe precipitated crystals are filtered
washwashed with icecold water
customThe crude product obtained
customis recrystallized from 100 ml of acetonitrile
filtrationThe crystals are filtered
washwashed with acetonitrile and ether
customdried

Sources & evidence

ORD record: ord-bf86d3148f0e42579be2b8d53c752cda
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053082B1

Reaction notes

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