p-Toluenesulfonic acid → HCID 15655149, compound

HRID 2067983Notes

Reaction equation

HRID 2067983 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][C:5](=O)[CH2:6][O:7][CH3:8].[CH3:11]OC(OC)N(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][NH2:39])=[CH:34][CH:33]=1>C(#N)C.C(N(CC)CC)C>[CH3:1][O:2][C:3]([C:4]1[CH:11]=[N:39][N:38]([C:35]2[CH:36]=[CH:37][C:32]([Cl:31])=[CH:33][CH:34]=2)[C:5]=1[CH2:6][O:7][CH3:8])=[O:10]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 123500Methyl 4-methoxyacetoacetate

Product 1

HCID 15655149HCID 15655149, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

4-Methoxy-3-oxobutyric acid methyl ester (1.50 g, 10.3 mmol) was mixed with dimethylformamide dimethylacetal (1.83 g, 15.4 mmol) and a catalytic amount of para-toluene sulfonic acid and heated in the microwave for 15 min at 130° C. The mixture was cooled to room temp. and then concentrated in vacuo to afford a red oil. In a second flask para-chlorophenylhydrazine hydrochloride (1.84 g, 10.3 mmol) was placed in acetonitrile (10 mL) and then treated with the above red oil in triethylamine (6 mL). The mixture was stirred for 14 h, concentrated in vacuo and purified by silica chromatography (5% ethylacetate in hexanes) to afford 1-(4-Chloro-phenyl)-5-methoxymethyl-1H-pyrazole-4-carboxylic acid methyl ester (1.90 g, 66%).

Workup

  1. temperatureThe mixture was cooled to room temp.
  2. concentrationconcentrated in vacuo
  3. customto afford a red oil
  4. concentrationconcentrated in vacuo
  5. custompurified by silica chromatography (5% ethylacetate in hexanes)

Sources & evidence

ORD record
ord-e22538fc9fab426a82c94975b3743b4f
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

Loading…