Oxalyl chloride → 3-[5-(2-Fluorophenyl)-[1,2,4]oxadiazol-3-yl]benzoyl chloride

HRID 920883

反応式

HRID 920883 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16](O)=[O:17])[N:9]=1.C(Cl)(=O)C([Cl:25])=O>CN(C)C=O.ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([Cl:25])=[O:17])[N:9]=1

参加物

5

反応物 2

HCID 65578Oxalyl chlorideHCID 11219835Ataluren2 回

生成物 1

HCID 578225233-[5-(2-Fluorophenyl)-[1,2,4]oxadiazol-3-yl]benzoyl chloride収率 97%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Compound 25 of the present invention may be prepared according to Scheme A as follows. A slurry of 3-[5-(2-fluorophenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid (Compound A1, 15.0 g; 52.8 mmol) and 100 μL of dimethylformamide catalyst in 250 mL of anhydrous dichloromethane is allowed to cool to 0° C. Oxalyl chloride (9.2 mL, 105.5 mmol, 2.0 eq.) is added to this slurry over 3 minutes. The reaction mixture is then allowed to warm to room temperature, and is stirred for 16 h. The resultant yellow solution is concentrated in vacuo, azeotroped several times with anhydrous dichloromethane (2×50 mL) and dried under high vacuum for 2 hrs to give 15.5 g of 3-[5-(2-fluorophenyl)-[1,2,4]oxadiazol-3-yl]benzoyl chloride (Compound A2) as a white solid (97%): 1H NMR (CDCl3) δ 7.23-7.38 (m, 2H), 7.58-7.71 (m, 2H), 8.22-8.29 (m, 2H), 8.50 (d, J=7.8 Hz, 1H), 8.91 (t, J=1.6 Hz, 1H).

後処理

  1. temperatureto warm to room temperature
  2. concentrationThe resultant yellow solution is concentrated in vacuo
  3. customazeotroped several times with anhydrous dichloromethane (2×50 mL)
  4. customdried under high vacuum for 2 hrs

出典と根拠

ORDレコード
ord-813452940c7e49dea8c0e5b5c4526af0
出典データセット
uspto-grants-2016_03
特許番号
US09273076B2

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