Thionyl Chloride → 4-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoyl chloride

HRID 1178249ノート

反応式

HRID 1178249 の反応式
[O:1]=[C:2]1[C:6]2[N:7]=[N:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]=2[NH:4][N:3]1[C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=1.S(Cl)([Cl:26])=O>>[O:1]=[C:2]1[C:6]2[N:7]=[N:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]=2[NH:4][N:3]1[C:15]1[CH:23]=[CH:22][C:18]([C:19]([Cl:26])=[O:20])=[CH:17][CH:16]=1

参加物

3

反応物 2

HCID 24386Thionyl ChlorideHCID 589749144-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoic acid

生成物 1

HCID 589748734-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoyl chloride

実験手順

Thionyl chloride (90 ml) was added to 4-(3-oxo-1,3-dihydro-2H-pyrazolo-[4,3-c]cinnolin-2-yl)benzoic acid (2.36 g, 7.70 mmol). The mixture was heated to reflux for 2 h under nitrogen atmosphere. A dark red solution was obtained, cooled to room temperature and excess thionyl chloride was removed under vacuum. Toluene (30 ml) was added to the residues and the mixture was stirred at room temperature under nitrogen atmosphere until precipitation was complete. The solids were collected by filtration and washed with toluene (2×30 ml). The title compound was isolated as a red solid (2.20 g, 6.77 mmol, 88%) LCMS: m/z 321 [M+H]+ (methyl ester resulting from sample make-up in methanol).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h under nitrogen atmosphere
  3. customA dark red solution was obtained
  4. customexcess thionyl chloride was removed under vacuum
  5. additionToluene (30 ml) was added to the residues
  6. filtrationThe solids were collected by filtration
  7. washwashed with toluene (2×30 ml)

出典と根拠

ORDレコード
ord-52f4bac1e2494535a9f03b9949f717b7
出典データセット
uspto-grants-2007_10
特許番号
US07276505B2

反応ノート

読み込み中…