Phosphorus sulfide (P2S5) → HCID 21957865, compound

HRID 1994062Notes

Reaction equation

HRID 1994062 reaction equation
[CH3:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([C:16]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][N:18]([CH3:25])[CH:17]=1)=O)[CH2:3][CH:4]([CH3:6])[CH3:5].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27]>O1CCOCC1>[CH3:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([C:16]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][N:18]([CH3:25])[CH:17]=1)=[S:27])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 21957868HCID 21957868, compound

Product 1

HCID 21957865HCID 21957865, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
72.5 °C

Procedure

In a sulfonation flask a mixture of 0.6 g 1-Methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid[2-(1,3-dimethylbutyl)phenyl]amide, 0.45 g P2S5 and 30 ml dioxane is heated at 70-75° C. for 3 hours. After filtration, the solvent is removed in a water jet vacuum and the residue taken up in ethylacetate. The organic phase is washed twice with water and ethylacetate is removed in a water jet vacuum. The crude material is purified by column chromatography over silica gel (eluant:ethylacetate/n-hexane=1:1). Yield: 0.53 g 1-Methyl-4-trifluoromethyl-1H-pyrrole-3-carbothioic acid[2-(1,3-dimethylbutyl)phenyl]amide in the form of a reddish resin (1H-NMR).

Workup

  1. filtrationAfter filtration
  2. customthe solvent is removed in a water jet vacuum
  3. washThe organic phase is washed twice with water and ethylacetate
  4. customis removed in a water jet vacuum
  5. customThe crude material is purified by column chromatography over silica gel (eluant:ethylacetate/n-hexane=1:1)

Sources & evidence

ORD record
ord-05bdfaaa2279487b9a7d486e9bc1f637
Source dataset
uspto-grants-2010_01
Patent number
US07652059B2

Reaction notes

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