Dimethylformamide → 2-Chloro-4-fluoro-5-[4-formyl-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester

HRID 1379818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1379818
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[C:16]([CH:17]=[O:18])=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[N:13]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:24](Cl)(=O)[C:25](Cl)=O.[CH3:30]N(C=O)C>C(Cl)Cl.CC(O)C>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[C:16]([CH:17]=[O:18])=[C:15]([C:19]([F:20])([F:21])[F:22])[N:14]([CH3:23])[N:13]=2)=[CH:7][C:3]=1[C:4]([O:6][CH:24]([CH3:25])[CH3:30])=[O:5]

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 229064152-chloro-4-fluoro-5-[4-formyl-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid

Produkt 1

HCID 572606202-Chloro-4-fluoro-5-[4-formyl-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a slurry of 2.5 g of 2-chloro-4-fluoro-5-[4-formyl-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid (Ex. 3) in 50 ml of methylene chloride was added 10 mL of oxalyl chloride followed by catalytic DMF. The solution was stirred for one hour and concd in vacuo. The resultant residue was diluted in 2-propanol and heated to 50° C. for one hour. The reaction was poured onto water and extracted into diethyl ether. The combined organic extracts were washed with brine and 2.5N sodium hydroxide solution, dried and concd to give a material which contained the desired product and a bi-product. Chromatographic purification (silica, 10% ethyl acetate in hexanes) afforded 1.0 g of 2-chloro-4-fluoro-5-[4-formyl-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester in a 36% yield: mp 90° C.; 1HNMR (CDCl3) δ 10.04 (s, 1H), 7.9 (d, 1H, J=7.6), 7.25 (d, 1H, J=9.2), 5.23 (m, 1H), 4.11 (s, 3H), 1.35 (d, 6H, J=6.0).

Aufarbeitung

  1. additionThe reaction was poured onto water
  2. extractionextracted into diethyl ether
  3. washThe combined organic extracts were washed with brine and 2.5N sodium hydroxide solution
  4. customdried
  5. customto give a material which

Quellen und Nachweise

ORD-Eintrag
ord-01eb3c2b315c4ad580684d5eebe3c08a
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05672715

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