Water → HCID 19754686, compound

HRID 908100Notes

Reaction equation

HRID 908100 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[CH:15]12[CH2:21][CH:18]([CH2:19][CH2:20]1)[CH2:17][CH:16]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:29]([C:31]1[C:32]([CH:37]([F:39])[F:38])=[N:33][N:34]([CH3:36])[CH:35]=1)=O.O.C1CCCCC1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH:15]12[CH2:21][CH:18]([CH2:19][CH2:20]1)[CH2:17][CH:16]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:29]([C:31]1[C:32]([CH:37]([F:39])[F:38])=[N:33][N:34]([CH3:36])[CH:35]=1)=[S:2]

Participants

6

Reactant 4

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 21867204Cyclohexane ethylacetateHCID 67412583HCID 67412583, compound

Product 1

HCID 19754686HCID 19754686, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

0.3 g (1.4 mmol) of phosphorus pentasulphide is added to a solution consisting of 0.48 g (1.4 mmol) of N-(2-bicyclo[2.2.1]hept-2-ylphenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide in 20 ml of toluene, and the reaction mixture is stirred at 70° C. for 2 hours. For work-up, the reaction mixture is poured into water and extracted once with 20 ml of toluene and twice with in each case 20 ml of ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. Column chromatography (gradient cyclohexane/ethyl acetate) gives 0.32 g (0.89 mmol, 63% of theory) of N-(2-bicyclo[2.2.1]hept-2-ylphenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-thiocarboxamide [logP (pH 2.3)=3.66].

Workup

  1. extractionextracted once with 20 ml of toluene and twice with in each case 20 ml of ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4da1b2fd69834001a6ab96812bb94567
Source dataset
uspto-grants-2011_09
Patent number
US08017558B2

Reaction notes

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