Water → HCID 178525493, compound

HRID 1741009Notes

Reaction equation

HRID 1741009 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([NH:12][C:13]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[C:16]([S:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][C:36]#N)=[CH:28][CH:27]=2)[NH:15][N:14]=1)(=[O:11])=[O:10].[OH2:38].[OH-:39].[K+].[Cl-].[NH4+]>C(O)COCCO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[S:9]([NH:12][C:13]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[C:16]([S:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][C:36]([OH:39])=[O:38])=[CH:28][CH:27]=2)[NH:15][N:14]=1)(=[O:10])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 178511056HCID 178511056, compound

Product 1

HCID 178525493HCID 178525493, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

The 3-(2,6-dichlorophenyl)sulfonylamino-4-(2-pyridyl)-5-(4-(3-cyanopropoxy)benzylthio)-(1H)-pyrazole (0.19 g), prepared as described in Example 7, above, in 2 ml of diethylene glycol and 0.2 ml of water with 0.1 g of potassium hydroxide was heated at 100° C. overnight. After cooling, the reaction was poured into a saturated solution of ammonium chloride, extracted in tetrahydrofuran/ethyl acetate 1:1, and washed with water and then brine. The organic phase was dried over MgSO4, filtered and concentrated to dryness. The residue was treated with ethanol/ether 2:1 to precipitate a yellow solid (0.130 g, 66% yield) isolated by filtration.

Workup

  1. temperatureAfter cooling
  2. extractionextracted in tetrahydrofuran/ethyl acetate 1:1
  3. washwashed with water
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. additionThe residue was treated with ethanol/ether 2:1

Sources & evidence

ORD record
ord-2000957f307b4e26b6e364d378df49e2
Source dataset
uspto-grants-1999_10
Patent number
US05972972

Reaction notes

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