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

HRID 600760

반응식

HRID 600760 반응식
[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

참가 물질

5

반응물 2

HCID 65578Oxalyl chlorideHCID 11219835Ataluren2회

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-54c0da07b7874850b1b5b825fcbc15d1
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902235B2

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