Water → 7-Iodo-3,4-dihydro-1H-benzo[b]azepine-2,5-dione

HRID 2373359Notes

Reaction equation

[I:1][C:2]1[CH:19]=[CH:18][C:5]2[NH:6][C:7](=[O:17])[CH2:8][CH:9](C(OCC)=O)[C:10](=[O:11])[C:4]=2[CH:3]=1.[Na+].[Cl-].O>CS(C)=O>[I:1][C:2]1[CH:19]=[CH:18][C:5]2[NH:6][C:7](=[O:17])[CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of ethyl 7-iodo-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylate (iii-a) (4.84 g, 13.2 mmol) in dimethyl sulfoxide (66 mL) was added a solution of NaCl (81 mg, 15.9 mmol) in H2O (475 μL, 26.4 mmol). The reaction mixture was heated to 150° C. for 2 h, and subsequently cooled to 0° C. for 30 min. H2O (120 mL) was added and the solution was allowed to stir for an additional 1.5 h at 0° C. The resulting precipitate was filtered to provide iv-a (3.2 g, 81%) as a purple/brown solid: MS m/z═302 (M+H).

Workup

temperaturesubsequently cooled to 0° C. for 30 min
filtrationThe resulting precipitate was filtered
customto provide iv-a (3.2 g, 81%) as a purple/brown solid

Sources & evidence

ORD record: ord-d7eedc1188114d328c1eae1aace8f4ba
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459448B2

Reaction notes

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