Water → 1H-imidazole-2-carbothioic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amide

HRID 1244382Notes

Reaction equation

HRID 1244382 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[NH:15][C:16]([C:18]1[NH:19][CH:20]=[CH:21][N:22]=1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[NH:15][C:16]([C:18]1[NH:19][CH:20]=[CH:21][N:22]=1)=[S:32]

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 865950081H-Imidazole-2-carboxylic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amide

Product 1

HCID 865950071H-imidazole-2-carbothioic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amideYield 41.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.41 g of 1H-Imidazole-2-carboxylic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amide (1.36 mmol) were taken up in toluene (25.0 ml) and treated with 1.65 g of Lawesson reagent (4.08 mmol). The reaction mixture was heated to reflux for 16 h. After cooling to ambient temperature, water (25 ml) was added and the mixture was extracted 3 times with methylene chloride. The combined organic phases were dried on sodium carbonate, evaporated and the residue was dried under high vacuum to yield 0.179 g of 1H-imidazole-2-carbothioic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amide (41%) as a yellow solid; M.p.: 189–190° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 h
  3. extractionthe mixture was extracted 3 times with methylene chloride
  4. customThe combined organic phases were dried on sodium carbonate
  5. customevaporated
  6. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-fffc7c9d33f54f2da6b4e6f445da8c8f
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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