p-Fluoronitrobenzene → 2-(4-nitrophenoxy)-10H-phenothiazine

HRID 456860ノート

反応式

HRID 456860 の反応式
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1>CN(C=O)C>[N+:29]([C:26]1[CH:27]=[CH:28][C:23]([O:1][C:2]2[CH:15]=[CH:14][C:13]3[S:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[NH:5][C:4]=3[CH:3]=2)=[CH:24][CH:25]=1)([O-:31])=[O:30]

参加物

5

反応物 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 1060871310H-phenothiazin-2-ol

生成物 1

HCID 226463722-(4-nitrophenoxy)-10H-phenothiazine収率 83%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

1.1 g (5.11 mmol) of 2-hydroxy-10H-phenothiazine (J. Med. Chem. (1992) 35, 716), 1.34 g (9.71 mmol) of K2CO3 and 0.94 g (6.64 mmol) of 4-fluoro-1-nitrobenzene are mixed in 25 ml anhydrous DMF in a flask under argon atmosphere,. The reaction mixture is heated at 70° C. for 18 hours. The solvent is then evaporated off under vacuum and the residue is taken up in 50 ml of AcOEt and 50 ml of water. After agitation and decantation, the organic phase is washed with 50 ml of salt water. The organic solution is dried over MgSO4, filtered and concentrated under vacuum. The residue is crystallized from diisopropyl ether. After drying, a yellow solid is obtained with a yield of 83%. Melting point: 210–211° C.

後処理

  1. customThe solvent is then evaporated off under vacuum
  2. washAfter agitation and decantation, the organic phase is washed with 50 ml of salt water
  3. dry with materialThe organic solution is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue is crystallized from diisopropyl ether
  7. customAfter drying
  8. customa yellow solid is obtained with a yield of 83%

出典と根拠

ORDレコード
ord-0551a6aca7f34bda83aa22674463acaa
出典データセット
uspto-grants-2007_03
特許番号
US07186752B2

反応ノート

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