Lawesson's reagent → HCID 57642331, compound

HRID 2112496Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:21][CH3:22])=[CH:4][C:5]2[NH:11][C:10](=O)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:6]=2[CH:20]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>COCCOC>[Br:1][C:2]1[C:3]([O:21][CH3:22])=[CH:4][C:5]2[NH:11][C:10](=[S:32])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:6]=2[CH:20]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 2.0 g (0.0053 mole) of 7-bromo-5-(2-chlorophenyl)-1,3-dihydro-8-methoxy-2H-1,4-benzodiazepin-2-one (Id), 200 mL of 1,2-dimethoxyethane and 2.13 g (0.0053 mole) of Lawesson's reagent (2,4-bis(4-methoxyphenyl)-2,4-disulfide-1,3,2,4-dithiadiphosphetane) was heated at 85° C. for 1 hour, then cooled and poured onto ice cold sodium bicarbonate solution. The mixture was extracted twice with ethyl acetate-methanol (9:1), and the organic layers washed successively with water and brine. The combined extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Trituration of the residue with ethyl acetate provided 1.7 g of 7-bromo-5-(2-chlorophenyl)-1,3-dihydro-8-methoxy-2H-1,4-benzodiazepin-2-thione (IId). MH+/Z=395.

Workup

temperaturecooled
additionpoured onto ice cold sodium bicarbonate solution
extractionThe mixture was extracted twice with ethyl acetate-methanol (9:1)
washthe organic layers washed successively with water and brine
dry with materialThe combined extracts were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e2d081a1bc8e49a8b09fe44f05aa64c4
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524840B2

Reaction notes

Loading…