Water → HCID 9946867, compound

HRID 1611862Notes

Reaction equation

HRID 1611862 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[CH2:14][C:13]([C:23](O)=[O:24])=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].S(Cl)(Cl)=O.[OH-].[NH4+:31].O>O1CCCC1.CO>[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)[CH2:14][C:13]([C:23]([NH2:31])=[O:24])=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 9968787HCID 9968787, compound

Product 1

HCID 9946867HCID 9946867, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1-(4-aminosulphonylphenyl)-4,5-dihydro-5-(4-methylphenyl)-1H-pyrazole-3-carboxylic acid (3.7 g, 10.3 mmoles) and thionyl chloride (3 g, 25.8 mmoles) are dissolved in 70 ml of tetrahydrofuran and shaken at room temperature for 16 hours. The mixture is evaporated to dryness with a rotavapour and the crude acid chloride so obtained dissolved in 30 ml of methanol in a globe of inert atmosphere and cooled to 0° C. 9 ml of concentrated ammonium hydroxide solution dissolved in 20 ml of THF is added. The mixture is shaken at room temperature for 16 hours and the solvent eliminated with the rotavapor. Water is added to the residue and the mixture extracted with ethyl acetate, which is washed with water, dried over anhydrous sodium sulphate and evaporated to dryness. The crude residue so obtained is crystallised from ethyl acetate-petrol ether to give 2.6 g (yield: 72%) of the desired compound with a m.p.=210-5° C.

Workup

  1. customThe mixture is evaporated to dryness with a rotavapour
  2. customthe crude acid chloride so obtained
  3. temperaturecooled to 0° C
  4. additionis added
  5. stirringThe mixture is shaken at room temperature for 16 hours
  6. extractionthe mixture extracted with ethyl acetate, which
  7. washis washed with water
  8. dry with materialdried over anhydrous sodium sulphate
  9. customevaporated to dryness
  10. customThe crude residue so obtained
  11. customis crystallised from ethyl acetate-petrol ether

Sources & evidence

ORD record
ord-c85f992f69194ca28ef2d6011a9a2509
Source dataset
uspto-grants-2006_01
Patent number
USRE038963E1

Reaction notes

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