Lawesson's reagent → HCID 58423803, compound

HRID 2096401Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[NH:14][C:13](=O)[NH:12]3)[CH2:10][CH:9]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=3[F:25])[O:8][C:5]2=[CH:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>C1(C)C=CC=C(C)C=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[NH:14][C:13](=[S:35])[NH:12]3)[CH2:10][CH:9]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=3[F:25])[O:8][C:5]2=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 6-bromo-2-(2,3-difluorophenyl)spiro[chroman-4,4′-imidazolidine]-2′,5′-dione (212 mg, 0.52 mmol) and Lawesson's Reagent (201 mg, 0.52 mmol) in dry m-xylene (4.5 mL) was heated at 150° C. in a 10 mL CEM microwave test tube for 25 minutes. The mixture was concentrated in vacuo and the residue was purified by preparative TLC to give 6-bromo-2-(2,3-difluorophenyl)-2′-thioxospiro[chroman-4,4′-imidazolidine]-5′-one (163 mg, 74%). 1H-NMR (CDCl3): 2.33 (t, 3H), 2.54 (d, 1H), 5.36 (s, 1H), 6.17 (d, 1H), 6.91 (d, 1H), 7.17 (m, 3H), 7.30 (m, 2H), 7.46 (s, 1H).

Workup

concentrationThe mixture was concentrated in vacuo
customthe residue was purified by preparative TLC

Sources & evidence

ORD record: ord-22b44d9039c4458eb994e895fec98dcf
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450308B2

Reaction notes

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