Water → 1-(2-Methoxy-4-(trifluoromethyl)phenyl)phthalazine-6-sulfonyl chloride

HRID 1473403노트

반응식

HRID 1473403 반응식
C(S[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[O:29][CH3:30])=[N:14][N:13]=[CH:12]2)C1C=CC=CC=1.O.[Cl:32]N1C(C)(C)C(=O)N(Cl)C1=O.[O-:43][S:44]([O-:47])(=O)=O.[Mg+2]>CC#N.C(O)(=O)C.C(Cl)Cl>[CH3:30][O:29][C:20]1[CH:21]=[C:22]([C:25]([F:26])([F:28])[F:27])[CH:23]=[CH:24][C:19]=1[C:15]1[C:16]2[C:11](=[CH:10][C:9]([S:44]([Cl:32])(=[O:47])=[O:43])=[CH:18][CH:17]=2)[CH:12]=[N:13][N:14]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 24083Sulfuric acid magnesium salt (1:1)HCID 866874486-(Benzylthio)-1-(2-methoxy-4-(trifluoromethyl)phenyl)phthalazine

생성물 1

HCID 866874491-(2-Methoxy-4-(trifluoromethyl)phenyl)phthalazine-6-sulfonyl chloride수율 62.3%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

A solution of 6-(benzylthio)-1-(2-methoxy-4-(trifluoromethyl)phenyl)phthalazine 2 (0.340 g, 0.797 mmol) in 20 mL of MeCN, 0.75 mL of acetic acid, and 0.5 mL of water (20/0.75/0.5 ratio) was cooled to 0° C. and was treated with 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.314 g, 1.595 mmol). After stirring for one hour, LC/MS showed mostly product, so the reaction mixture was diluted with DCM and was treated with MgSO4. After stirring for 10 minutes, the reaction mixture was filtered and concentrated. Purification of the crude residue by silica gel column chromatography (0 to 40% EtOAc/heptane) gave 1-(2-methoxy-4-(trifluoromethyl)phenyl)phthalazine-6-sulfonyl chloride (0.200 g, 0.497 mmol, 62.3% yield).

후처리

  1. stirringAfter stirring for 10 minutes
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. customPurification of the crude residue by silica gel column chromatography (0 to 40% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-9551b58396704260982528961a5df666
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

반응 노트

불러오는 중…