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

HRID 1178249노트

반응식

HRID 1178249 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-52f4bac1e2494535a9f03b9949f717b7
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276505B2

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