Pyridine → 9-Chloro-11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 2351378Notes

Reaction equation

[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[NH:7][C:8]3[CH:14]=[CH:13][CH:12]=[N:11][C:9]=3[NH:10][C:4]=2[CH:3]=1.N1C=CC=CC=1.[C:24](Cl)([Cl:26])=[O:25]>O1CCOCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[NH:7][C:8]3[CH:14]=[CH:13][CH:12]=[N:11][C:9]=3[N:10]([C:24]([Cl:26])=[O:25])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

11.6 g (0.0472 mol) of 9-chloro-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, suspended in a mixture of 450 ml of anhydrous dioxane and 6.4 ml (0.08 mol) of pyridine, were combined at 45° C., within 20 minutes, with 47.1 ml (0.094 mol) of a 20% solution of phosgene in toluene. The reaction mixture was stirred for 2 hours at 45° C. and then for 4 hours at 60° C. The mixture was filtered while hot, the filtrate was evaporated down in vacuo, the crystallising residue remaining was resuspended in 100 ml of dioxane, refluxed for 2 hours, evaporated down once more, mixed with copious amounts of water and suction filtered. After drying in a circulating air dryer the product had an m.p. of 265°-267° C., RF 0.70 (Macherey-Nagel, PolygramRSIL G/UV254, pre-coated plastic sheets for TLC, eluant: dichloromethane/ethyl acetate 1/1 v/v).

Workup

waitfor 4 hours at 60° C
filtrationThe mixture was filtered while hot, the filtrate
customwas evaporated down in vacuo
temperaturerefluxed for 2 hours
customevaporated down once more
additionmixed with copious amounts of water and suction
filtrationfiltered
customAfter drying in a circulating air dryer the product

Sources & evidence

ORD record: ord-23c745d391c64869be99aec449c60d39
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04873236

Reaction notes

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