Lawesson's reagent → HCID 58424149, compound

HRID 2096382Notes

Reaction equation

HRID 2096382 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]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[O:8][C:5]2=[CH:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[NH:14][C:13](=[S:33])[NH:12]3)[CH2:10][CH:9]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[O:8][C:5]2=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58424582HCID 58424582, compound

Product 1

HCID 58424149HCID 58424149, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 6-bromo-2-cyclohexylspiro[chroman-4,4′-imidazolidine]-2′,5′-dione (400 mg, 1.06 mmol) and Lawesson's Reagent (427 mg, 1.06 mmol) in dry 1,4-dioxane (6 mL) was heated at 120° C. in a 10 mL CEM microwave test tube for 30 minutes. The mixture was concentrated in vacuo and the residue was purified by preparative TLC to give 6-bromo-2-cyclohexyl-2′-thioxospiro[chroman-4,4′-imidazolidin]-5′-one (280 mg, 67%). 1H-NMR (CDCl3): 0.78-0.92 (m, 2H), 1.13 (m, 1H), 1.17-1.31 (m, 3H), 1.71 (m, 2H), 1.78 (m, 2H), 1.94 (d, 1H), 2.05 (t, 1H), 2.61 (d, 1H), 4.91 (m, 1H), 6.78 (d, 1H), 7.04 (s, 1H), 7.13 (s, 1H), 7.32 (d, 1H), 9.33 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-6d3a487d420e48428ace1f054e9394d4
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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