Lawesson's reagent → HCID 67432598, compound

HRID 410527Notes

Reaction equation

HRID 410527 reaction equation
[Si:1]([O:18][CH2:19][C:20]([CH3:37])([CH3:36])[C:21]([NH:23][CH2:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-:35])=[O:34])[CH:28]=1)=O)=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:47])=CC=1>C1(C)C=CC=CC=1>[Si:1]([O:18][CH2:19][C:20]([C:21]1[S:47][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-:35])=[O:34])[CH:28]=2)=[CH:24][N:23]=1)([CH3:37])[CH3:36])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67432873HCID 67432873, compound

Product 1

HCID 67432598HCID 67432598, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the product of Step 1 (680 mg, 1.31 mmol) in toluene (6.5 mL) was added Lawesson's reagent (530 mg, 1.31 mmol) and the mixture was heated to 100° C. for 20 hours and then cooled to it then the mixture was concentrated in vacuo. Purification by chromatography on silica gel (100:0 to 50:50, hexanes:ethyl acetate) provided 461 mg (0.892 mmol, 68%) of 2-(1-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropan-2-yl)-5-(3-nitrophenyl)-1,3-thiazole as a colorless viscous oil.

Workup

  1. temperaturecooled to it
  2. concentrationthe mixture was concentrated in vacuo
  3. customPurification by chromatography on silica gel (100:0 to 50:50, hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-6fe98255d3bc43dda1a3f14868778b7a
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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