Acetic Acid → HCID 18409499, compound

HRID 993322Notes

Reaction equation

HRID 993322 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:15][N:14]=[C:13]([O:16][CH2:17][C:18](=O)[C:19]([CH3:22])([CH3:21])[CH3:20])[C:12]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)(=O)C>C1(C)C=CC=CC=1>[C:19]([C:18]1[N:14]2[N:15]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[C:12]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[C:13]2[O:16][CH:17]=1)([CH3:21])([CH3:20])[CH3:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 18409498HCID 18409498, compound

Product 1

HCID 18409499HCID 18409499, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-(4-(methylsulphonyl)phenyl)-4-phenyl-3-trimethylacetylmethoxy-pyrazole prepared according to the Example 32B [(100 mg, 0.24 mmol), p-toluenesulfonic acid hydrate (25 mg) in toluene (40 mL), and acetic acid (15 mL) was refluxed using a Dean-Stark trap to remove water, for 12 hours. The reaction mixture was concentrated in vacuo and the residue chromatographed (silica gel, 1:1 hexane/ethyl acetate) to provide the desired product (yield: 97 mg; 99%). MP 187-180° C.; MS (APCI+) m/z 395 (M+H)+; (APCI−) m/z 393 (M−H)−, 429 (M+Cl)−; 1H NMR (300 MHz, DMSO-d6) δ1.49 (s, 9H), 3.25 (s, 3H), 7.35 (m, 5H), 7.76 (d, J=9 Hz, 2H), 7.95 (s+d, J=9 Hz, 3H); Anal. calc. for C22H22N2O3S.0.5 H2O: C, 65.48; H, 5.74; N, 6.94. Found: C, 65.70; H, 5.69; N, 6.65.

Workup

  1. customprepared
  2. temperaturewas refluxed
  3. customto remove water
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe residue chromatographed (silica gel, 1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7ee01b81edf84cab9c4034249564123c
Source dataset
uspto-grants-2002_10
Patent number
US06472416B1

Reaction notes

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