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Methyl iodide → 4-Bromo-2,3,7-trimethoxy-10H-phenothiazine

HRID 979092
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HRID 979092 반응식
[Br:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=3)[NH:7][C:6]=2[CH:5]=[C:4]([O:18][CH3:19])[C:3]=1[OH:20].CI.[C:23](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[Br:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=3)[NH:7][C:6]=2[CH:5]=[C:4]([O:18][CH3:19])[C:3]=1[O:20][CH3:23]
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참가 물질

7

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium Carbonate2회HCID 138537384-bromo-2,7-dimethoxy-3-hydroxy-10H-phenothiazine

생성물 1

HCID 138820384-Bromo-2,3,7-trimethoxy-10H-phenothiazine수율 36.7%

시약·촉매·용매 3

HCID 962Water용매HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-bromo-2,7-dimethoxy-3-hydroxy-10H-phenothiazine (3.54 g) and methyliodide (2.5 ml) in DMF (20 ml) there was added pulverized potassium carbonate (1.3 g). The reaction mixture was stirred at room temperature. After 15 minutes, another addition of potassium carbonate (1 gram) was made, followed by two other such additions at 15-minute intervals. The final mixture was stirred for a further 15 minutes, then it was diluted with water (100 ml) and ethyl acetate (100 ml). The organic layer was washed twice with water, dried and evaporated down to a solid residue. Crystallization from acetone followed by column chromatography on silica gel eluting with 1:19 ethyl acetate-dichloromethane afforded the pure title compound (1.27 g). m.p. 223°-225° C.

후처리

  1. waitfollowed by two other such additions at 15-minute
  2. washThe organic layer was washed twice with water
  3. customdried
  4. customevaporated down to a solid residue
  5. customCrystallization from acetone

출처 및 근거

ORD 기록
ord-e805811533434951985b0b30723bfce5
출처 데이터셋
uspto-grants-1987_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04666907

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