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

HRID 1672183Notes

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-1b271957783c448cbf78323f17dd3fae
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998952B2

Reaction notes

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