Diethyl Ether → 4-dimethylaminomethylene-7-iodo-3,4-dihydro-1H-benzo[b]azepine-2,5-dione

HRID 544985Notes

Reaction equation

[I:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7](=[O:12])[CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19].CCOCC>C1COCC1>[CH3:17][N:18]([CH:20]=[C:9]1[CH2:8][C:7](=[O:12])[NH:6][C:5]2[CH:13]=[CH:14][C:2]([I:1])=[CH:3][C:4]=2[C:10]1=[O:11])[CH3:19]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 7-iodo-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (iv-a) (1.67 g, 5.54 mmol) in THF (15 mL) was added dimethylformamide dimethylacetal (4.0 mL, 27.7 mmol) and the reaction mixture heated to 70° C. for 1 h. The reaction mixture was cooled to 22° C., treated with Et2O (50 mL), and the resulting precipitate filtered and dried in vacuo to give v-a (1.64 g, 83%) as a brown powder: MS m/z=357 (M+H).

Workup

temperatureThe reaction mixture was cooled to 22° C.
filtrationthe resulting precipitate filtered
customdried in vacuo
customto give v-a (1.64 g, 83%) as a brown powder

Sources & evidence

ORD record: ord-fc700df12b924d2f8a31c4b2a96a1431
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935694B2

Reaction notes

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