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

HRID 1378301ノート

反応式

HRID 1378301 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c28a3588a2fa42b8a0f8475a5073b4f1
出典データセット
uspto-grants-1997_09
特許番号
US05668088

反応ノート

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