Lawesson's reagent → HCID 19421392, compound

HRID 743998Notes

Reaction equation

HRID 743998 reaction equation
[CH2:1]([C:5]1[N:6]([O:27][CH2:28][O:29][CH:30]([Si:32]([CH3:35])([CH3:34])[CH3:33])[CH3:31])[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][CH2:24][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:45]2)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([C:5]1[N:6]([O:27][CH2:28][O:29][CH:30]([Si:32]([CH3:35])([CH3:34])[CH3:33])[CH3:31])[C:7]([C:10](=[S:45])[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][CH2:24][CH3:25])=[O:22])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 19421373HCID 19421373, compound

Product 1

HCID 19421392HCID 19421392, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-n-Butyl-5-(2-ethoxycarbonylmethoxy-4-methoxybenzoyl)-1-trimethylsilylethyloxymethoxy-1H-imidazole(475 mg, 0.97 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) (215 mg, 0.532 mmol) and the solution heated to 80° for 1 h under argon. The reaction was cooled and the toluene solution applied directly to a silica gel column. Elution with 25-30% EtOAc/hexanes afforded the title compound as a deep purple-blue oil. (316 mg, 64% ).

Workup

  1. temperaturethe solution heated to 80° for 1 h under argon
  2. temperatureThe reaction was cooled
  3. washElution with 25-30% EtOAc/hexanes

Sources & evidence

ORD record
ord-3831206c220242dc9a8ee93c054fe2ed
Source dataset
uspto-grants-1996_09
Patent number
US05559105

Reaction notes

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