Lawesson's reagent → HCID 54394123, compound

HRID 324223Notes

Reaction equation

HRID 324223 reaction equation
[CH3:1][C:2]1([CH3:33])[CH2:11][CH:10]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:8]2[CH:7]=[C:6]([C:19]([NH:21][C:22]3[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=3)=O)[CH:5]=[CH:4][C:3]1=2.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:43]2)=CC=1>C1C=CC=CC=1>[CH2:29]([O:28][C:26](=[O:27])[C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:19]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:1])([CH3:33])[CH2:11][CH:10]=[C:9]([C:12]4[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=4)[C:8]=3[CH:7]=2)=[S:43])=[CH:32][CH:31]=1)[CH3:30]

Participants

4

Reactant 2

HCID 87949Lawesson's reagent2×HCID 10836809HCID 10836809, compound2×

Product 1

HCID 54394123HCID 54394123, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 110.0 mg (0.25 mmol) ethyl 4-[[(5,6-dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenyl)carbonyl]amino]-benzoate (Compound 35) and 121.0 mg (0.30 mmol) of [2,4-bis(4-methoxyphenyl)- 1,3-dithia-2,4-diphosphetane-2,4-disulfide] (Lawesson's Reagent) in 12.0 ml of benzene was refluxed overnight. Upon cooling to room temperature, the mixture was filtered and the filtrate concentrated under reduced pressure. The title compound was isolated by column chromatography (10 to 25% EtOAc/hexanes) as a yellow solid. 1H NMR (CDCl3): δ 8.92 (1H, s), 8.06 (2H, t, J=8.5 Hz), 7.88-7.70 (3H, m), 7.42 (2H, d, J=8.1 Hz), 7.18 (4H, m), 6.03 (1H, t, J=4.7 Hz), 4.37 (2H, q, J=7.1 Hz), 2.38 (3H, s), 2,36 (2H, d, J=4.7 Hz), 1.56 (3H, t; J=7.1 Hz), 1.35 (6H, s).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-42f8772a79e84eac8570a335b62ca869
Source dataset
uspto-grants-2001_04
Patent number
US06218128B1

Reaction notes

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