Lawesson's reagent → 2-(4,5-Dihydro-thiazol-2-yl)-7-nitro-1H-indole

HRID 1515268Notes

Reaction equation

HRID 1515268 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[N+:16]([O-:18])=[O:17])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>ClC(Cl)C.C1(C)C=CC=CC=1>[S:28]1[CH2:2][CH2:3][N:4]=[C:5]1[C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 866443587-Nitro-1H-indole-2-carboxylic acid (2-chloro-ethyl)-amide

Product 1

HCID 579015982-(4,5-Dihydro-thiazol-2-yl)-7-nitro-1H-indoleYield 60%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

7-Nitro-1H-indole-2-carboxylic acid (2-chloro-ethyl)-amide (267 mg, 1 mmol) prepared in Step B was dissolved in dichloroethane (10 mL) and toluene (10 mL), and Lawesson's Reagent (1.29 g, 3.2 mmol) was added thereto. The mixture was refluxed for 4 h, and distilled under reduced pressure. Water was added thereto, and the reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and the concentrate was purified by column chromatography to give the title compound as a product of the cyclization reaction (148 mg, Yield 60%).

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. distillationdistilled under reduced pressure
  3. additionWater was added
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationThe filtrate was distilled under reduced pressure
  8. customthe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-c9b1310144d74e7a917bd898cc4d886b
Source dataset
uspto-grants-2012_07
Patent number
US08222414B2

Reaction notes

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