Lawesson's reagent → HCID 86718497, compound

HRID 1485408Notes

Reaction equation

COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:43](=[O:44])[C:35]3([CH2:37][CH:36]3[C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:34](=O)[NH:33][C:32]3[CH:46]=[CH:47][CH:48]=[CH:49][C:31]2=3)=[CH:26][CH:25]=1>C1COCC1>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:43](=[O:44])[C:35]3([CH2:37][CH:36]3[C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:34](=[S:10])[NH:33][C:32]3[CH:46]=[CH:47][CH:48]=[CH:49][C:31]2=3)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Lawesson's Reagent (237 mg, 0.58 mmol) was added to a solution of ethyl 1-(4-chlorophenyl)-2,4-dioxo-1,2,4,5-tetrahydrospiro[benzo[b][1,4]diazepine-3,1′-cyclopropane]-2′-carboxylate (150 mg, 0.39 mmol) in THF (20 mL). The resulting mixture was heated at 80° C. overnight. The solution was evaporated and purified by CombiFlash (PE:EA=1:1) to get ethyl 1-(4-chlorophenyl)-2-oxo-4-thioxo-1,2,4,5-tetrahydrospiro[benzo[b][1,4]diazepine-3,1′-cyclopropane]-2′-carboxylate (70 mg, 45%) as brown solid. LRMS (M+H)+: 400 m/z. 1H NMR (300 MHz, CDCl3): δ 0.96-1.04 (t, J=7.2 Hz, 3H), 1.19-1.25 (m, 1H), 1.70-1.76 (m, 1H), 2.17-2.19 (m, 1H), 3.73-3.96 (m, 2H), 6.68-6.71 (d, 1H, J=8.1 Hz), 7.11-7.12 (m, 1H), 7.14-7.24 (m, 4H), 7.24-7.26 (m, 2H).

Workup

customThe solution was evaporated
custompurified by CombiFlash (PE:EA=1:1)

Sources & evidence

ORD record: ord-ab754e3006534099906f97341a7997a8
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422292B2

Reaction notes

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