Lawesson's reagent → HCID 54482180, compound

HRID 743993Notes

Reaction equation

HRID 743993 reaction equation
[CH2:1]([C:5]1[N:6]([CH3:29])[C:7]([C:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:39]2)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([C:5]1[N:6]([CH3:29])[C:7]([C:10](=[S:39])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 54415455HCID 54415455, compound

Product 1

HCID 54482180HCID 54482180, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-n-Butyl-1-methyl-5-(2-t-butoxycarbonylmethoxy-4-methoxybenzoyl)-1H-imidazole (465 mg, 1.16 mmol) dissolved in toluene (5 ml) was mixed with 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) (258 mg, 0.638 mmol) and the solution heated to 95° for 1 h under argon. The reaction was cooled and the toluene solution applied directly to a silica gel column. Elution with 50% EtOAc/hexanes afforded the title compound as a deep purple-green solid. (206 mg, 53%).

Workup

  1. temperaturethe solution heated to 95° for 1 h under argon
  2. temperatureThe reaction was cooled
  3. washElution with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-a343691881014f9cada81fb05a267391
Source dataset
uspto-grants-1996_09
Patent number
US05559105

Reaction notes

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