Ethyl 3-(m-nitrophenyl)-3-oxopropionate → HCID 10447091, compound

HRID 1062676Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([C:10](=O)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].OC1C(OS(C2C=CC(C)=CC=2)(=O)=O)=C(I)C=CC=1.[NH2:37][C:38]([NH2:40])=[S:39]>C(#N)C>[NH2:40][C:38]1[S:39][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:37]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of ethyl 3-(3-nitrophenyl)-3-oxopropionate (3.45 g, 14.5 mmol) in 100 mL of acetonitrile was added hydroxy(tosyloxy)iodobenzene (6.3 g, 16.0 mmol). The resulting suspension was stirred at 65° C. for 1 h at which time the reaction was a homogeneous solution. Thiourea (1.22 g, 16.0 mmol) was added and stirring was continued at 65° C. for 2 h. The mixture was cooled and concentrated, and the residue was taken up in ethyl acetate, washed with saturated aq Na2CO3 and brine, dried (MgSO4) and concentrated. The residue was triturated with ethyl ether to afford 3.0 g (71%) of the title compound as a yellow solid. 1H NMR (DMSO-d6) δ: 8.47 (t, 1H, J=1.9 Hz); 8.24 (m, 1H) ; 8.21 (m, 1H); 7.97 (broad s, 2H); 7.65 (t, 1H, J=8.1 Hz); 4.08 (q, 2H, J=7.1 Hz); 1.11 (t, 3H, J=7.1 Hz).

Workup

stirringstirring
waitwas continued at 65° C. for 2 h
temperatureThe mixture was cooled
concentrationconcentrated
washwashed with saturated aq Na2CO3 and brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was triturated with ethyl ether

Sources & evidence

ORD record: ord-50334582c9e0479cb76d25cdb644e3ba
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06962935B2

Reaction notes

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