Phenol → 5,6-Dihydroimidazo[4,5,1-jk][1]benzazepine-2,7(1H,4H)-dione

HRID 1381093Notes

Reaction equation

C([N:8]1[C:17]2=[CH:18][CH:19]=[CH:20][C:15]3=[C:16]2[N:10]([CH2:11][CH2:12][CH2:13][C:14]3=[O:21])[C:9]1=[O:22])C1C=CC=CC=1.OP(O)(O)=O.C1(O)C=CC=CC=1.[OH-].[Na+]>C(Cl)Cl.O>[NH:8]1[C:17]2=[CH:18][CH:19]=[CH:20][C:15]3=[C:16]2[N:10]([CH2:11][CH2:12][CH2:13][C:14]3=[O:21])[C:9]1=[O:22]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 29.2 g of the product of Step C, 292 g of o-phosphoric acid and 14.1 g of phenol were heated at 150° C. under an inert atmosphere for 2 hours, was cooled to about 35° C. and was poured into 1200 ml of iced water with stirring. 2 liters of methylene chloride were added to the mixture which was then made alkaline with sodium hydroxide. The mixture was filtered and the solids were washed with methylene chloride. The combined organic phases were washed, dried and evaporated to dryness under reduced pressure. The residue was crystallized and was chromatographed over silica gel. Elution with a 90-2-2 ethyl acetate-methanol-triethylamine mixture yielded 9.7 g of 5,6-dihydro-imidazo[4,5,l-j-k][1]benzazepin-2,7-[1H,4H]-dione melting at 235° C.

Workup

temperaturewas cooled to about 35° C.
filtrationThe mixture was filtered
washthe solids were washed with methylene chloride
washThe combined organic phases were washed
customdried
customevaporated to dryness under reduced pressure
customThe residue was crystallized
customwas chromatographed over silica gel
washElution with a 90-2-2 ethyl acetate-methanol-triethylamine mixture

Sources & evidence

ORD record: ord-3592415a675c4f1f956dc8614b094545
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04585770

Reaction notes

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