Lawesson's reagent → HCID 59580850, compound

HRID 2199191Notes

Reaction equation

[CH3:1][NH:2][C:3]([CH:5]([NH:7][C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[N:11][CH:10]=1)[CH3:6])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>ClCCCl>[CH3:1][NH:2][C:3]1[S:25][C:8]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:7][C:5]=1[CH3:6]

Participants

Conditions

Temperature: 130 °C

Procedure

To a 10 mL microwave vessel containing DCE (5 mL) was added N-(1-methylcarbamoyl-ethyl)nicotinamide (207 mg, 1.0 mmol) followed by Lawesson's reagent (2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide, 404 mg, 1.0 mmol) in one portion. The heterogeneous mixture was heated in a microwave for 5 min at 130° C. The reaction mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate (NaHCO3). The layers were separated and the organic layer was washed once with brine. The solution was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography (ethyl acetate) to give the desired product as an orange solid (141 mg, 68%): mp 84-87° C.; 1H NMR (300 MHz, CDCl3) δ 8.98 (d, J=1.7 Hz, 1H), 8.51 (dd, J=4.9, 1.7 Hz, 1H), 8.08 (dt, J=8.0, 1.7 Hz, 1H), 7.29 (m, 1H), 3.00 (s, 3H), 2.30 (s, 3H); ESIMS m/z 206.4 (M+1), m/z 204.2 (M−1).

Workup

customThe reaction mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate (NaHCO3)
customThe layers were separated
washthe organic layer was washed once with brine
dry with materialThe solution was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-d6679738ff424620a1ce18ff75d4c522
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09357780B2

Reaction notes

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