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

HRID 1378301노트

반응식

HRID 1378301 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c28a3588a2fa42b8a0f8475a5073b4f1
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668088

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