Acetic Anhydride → 1-Acetyl-2,3,5,6-tetrahydro-1H-benzo[b][1,5]diazocin-4-one

HRID 1687567Notes

Reaction equation

[NH:1]1[CH2:8][CH2:7][C:6](=[O:9])[NH:5][CH2:4][C:3]2[CH:10]=[CH:11][CH:12]=[CH:13][C:2]1=2.[C:14](OC(=O)C)(=[O:16])[CH3:15]>C(#N)C>[C:14]([N:1]1[CH2:8][CH2:7][C:6](=[O:9])[NH:5][CH2:4][C:3]2[CH:10]=[CH:11][CH:12]=[CH:13][C:2]1=2)(=[O:16])[CH3:15]

Participants

Conditions

Temperature: 80 °C

Procedure

2,3,5,6-Tetrahydro-1H-benzo[b][1,5]diazocin-4-one (prepared as in J. Am. Chem. Soc. 2004, 126, 3529-3533) (1.00 g, 5.68 mmol) was dissolved in anh acetonitrile (50 ml). Acetic anhydride (587 μL, 6.25 mmol) was added and the reaction mixture was heated to 80° C. for 16 h. The reaction mixture was concentrated, triturated with ether, and filtered to afford title compound as a beige solid. (1.063 g, 86%) mp 236-239° C.; LCMS: m/z=219.30 (M+H+), HPLC (95% purity); 1H NMR (400 MHz, DMSO-d6) δ 7.82 (m, 1H), 7.38 (m, 4H), 4.64 (m, 1H), 4.29 (m, 1H), 3.87 (m, 1H), 2.92 (m, 1H), 2.57 (m, 1H), 2.26 (m, 1H), 1.69 (s, 3H).

Workup

concentrationThe reaction mixture was concentrated
customtriturated with ether
filtrationfiltered

Sources & evidence

ORD record: ord-6f8b75e01a074e6299d32a20152a4dde
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148391B2

Reaction notes

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