Hydrochloric Acid → 8-iodo-2,3,4,5-tetrahydro-1H-1-benzazepine-2,5-dione

HRID 2387972Notes

Reaction equation

[I:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=[O:16])[CH:7](C(OC)=O)[CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.Cl>CS(C)=O.O>[I:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=[O:16])[CH2:7][CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of methyl 8-iodo-2,5-dioxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carboxylate (74 g, 0.2 mol) in DMSO (560 mL) and H2O (16 mL) was heated at 150° C. for 4 h. The reaction mixture was allowed to cool to rt, ice (1.0 L) was added, and the mixture was allowed to stir 12 h. To the flask was added 1N HCl (1.0 L) at 0° C. and the mixture allowed to stir for 3 h. The resulting precipitate was filtered and dried under reduced pressure to afford 8-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione (60 g, 97%).

Workup

temperatureto cool to rt
stirringto stir for 3 h
filtrationThe resulting precipitate was filtered
customdried under reduced pressure

Sources & evidence

ORD record: ord-d1c91e1f8944416685dbd768794dd58d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268992B2

Reaction notes

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