Sulfuric Acid → HCID 87551501、化合物

HRID 1169549

反応式

HRID 1169549 の反応式
[CH:1]1[C:23]2=[C:24]3[C:4]4[C:5]([CH:17]=[CH:18][C:19]3=[C:20](S([O-])(=O)=O)[CH:21]=[C:22]2[OH:25])=[C:6](S([O-])(=O)=O)[CH:7]=[C:8](S([O-])(=O)=O)[C:3]=4[CH:2]=1.[Na+:30].[Na+].[Na+].[OH:33][S:34](O)(=[O:36])=[O:35]>O>[OH:25][C:22]1[CH:21]=[CH:20][C:19]2[C:24]3=[C:4]4[C:5]([CH:6]=[CH:7][CH:8]=[C:3]4[C:2]([S:34]([O-:36])(=[O:35])=[O:33])=[CH:1][C:23]=13)=[CH:17][CH:18]=2.[Na+:30]

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 61388Pyranine

生成物 1

HCID 87551501HCID 87551501、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

Referring to Scheme 4, a 50-mL round bottom flask equipped with a magnetic stirring bar was charged with HPTS (9.5 mmols, 5 g) and 30% H2SO4 (35 mL). The mixture was heated at 150° C. for 20 min and then allowed to cool at ambient temp for 10 min. The solution was poured into 100 g of crushed ice and diluted to 200 mL with water. The mixture was extracted with isopropyl acetate (200 mL×4) and concentrated in vacuo. The residue was mixed with silica gel (3 g) and crushed into a fine powder and dry loaded onto a Biotage 40 M cartridge. The residue was purified via gradient elution using 5% MeOH: (5% NEt3:CH2Cl2) to 15% MeOH: (5% NEt3:CH2Cl2) to give the triethylamine salt of 1 (0.281 g). The salt was treated with 1 M HCl and extracted with isopropyl acetate and the isopropyl acetate layer dried over MgSO4 and concentrated in vacuo to give 1 as a brown/green foam. Synthesis of 1 was reported previously by E. Tietze and O. Bayer 1939 Ann 540:189-210. TLC (MeOH: CH2Cl2:NEt3, 2:7:1) Rf=0.23. 1H NMR (500 MHz, CD3OD) δ7.94 (t, J=7.6 Hz, 1H), 7.97 (d, J=9.4 Hz, 1H), 8.02 (d, J=9.2 Hz, 1H), 8.11 (t, J=7.7 Hz, 2H), 8.25 (s, 1H), 8.39 (d, J=9.1 Hz, 1H), 8.98 (d, J=9.3 Hz, 1H).

後処理

  1. customequipped with a magnetic stirring bar
  2. temperatureto cool at ambient temp for 10 min
  3. extractionThe mixture was extracted with isopropyl acetate (200 mL×4)
  4. concentrationconcentrated in vacuo
  5. additionThe residue was mixed with silica gel (3 g)
  6. customcrushed into a fine powder
  7. customdry
  8. customThe residue was purified via gradient elution

出典と根拠

ORDレコード
ord-a1c8457bc9304946aeaf37941d81cffe
出典データセット
uspto-grants-2010_11
特許番号
US07824918B2

関連ノート

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