Water → 5-(phenothiazin-3-ylideneamino)benzene-1,3-dicarboxylic Acid

HRID 440617ノート

反応式

HRID 440617 の反応式
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:15][C:16]1[CH:17]=[C:18]([C:25]([OH:27])=[O:26])[CH:19]=[C:20]([CH:24]=1)[C:21]([OH:23])=[O:22].O>CO.[N+]([O-])([O-])=O.[Ag+]>[C:21]([C:20]1[CH:24]=[C:16]([N:15]=[C:3]2[CH:4]=[C:5]3[C:14](=[N:13][C:12]4[C:7]([S:6]3)=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH:1]=[CH:2]2)[CH:17]=[C:18]([C:25]([OH:27])=[O:26])[CH:19]=1)([OH:23])=[O:22]

参加物

6

反応物 3

HCID 962WaterHCID 7108PhenothiazineHCID 668335-Aminoisophthalic acid

生成物 1

HCID 101504305-(phenothiazin-3-ylideneamino)benzene-1,3-dicarboxylic Acid収率 82.5%

試薬・触媒・溶媒 2

HCID 24470Silver Nitrate触媒HCID 887Methanol溶媒

反応条件

温度
10 °C

実験手順

Phenothiazine (1.0 g, 5.0 mmol) and 5-aminoisophthalic acid (0.9 g, 5.0 mmol) were dissolved in MeOH (200 mL), cooled to 10° C. and treated with 1 M aqueous AgNO3 (30 mL, 30 mmol). After stirring at 10° C. for 30 minutes H2O (40 mL) was added and stirring continued for an additional 5 minutes. The solid product was then collected by filtration and washed with H2O (50 mL). The solid was dissolved in MeOH (500 mL) containing concentrated aqueous NH4OH (10 mL), stirred for 20 minutes then filtered to remove Ag. The filtrate was concentrated to ca. half its original volume under reduced pressure and refrigerated overnight at 5° C. The mixture was then filtered through Celite (Celite Corp.) and concentrated in vacuo until solid began to separate. The resulting solution (ca. 100 mL) was again filtered through Celite, diluted with ethyl acetate (900 mL) and allowed to stand for 15 minutes. The red solid that separated was collected by filtration, washed with ethyl acetate and dried to give 18(1.55 g, 82.5%).

後処理

  1. additionwas added
  2. filtrationThe solid product was then collected by filtration
  3. washwashed with H2O (50 mL)
  4. dissolutionThe solid was dissolved in MeOH (500 mL)
  5. additioncontaining concentrated aqueous NH4OH (10 mL)
  6. stirringstirred for 20 minutes
  7. filtrationthen filtered
  8. customto remove Ag
  9. concentrationThe filtrate was concentrated to ca. half its original volume under reduced pressure and refrigerated overnight at 5° C
  10. filtrationThe mixture was then filtered through Celite (Celite Corp.)
  11. concentrationconcentrated in vacuo until solid
  12. customto separate
  13. filtrationThe resulting solution (ca. 100 mL) was again filtered through Celite
  14. additiondiluted with ethyl acetate (900 mL)
  15. waitto stand for 15 minutes
  16. customThe red solid that separated
  17. filtrationwas collected by filtration
  18. washwashed with ethyl acetate
  19. customdried

出典と根拠

ORDレコード
ord-7ed3dd3dd25e48038af575557903b3d8
出典データセット
uspto-grants-1996_05
特許番号
US05520786

反応ノート

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