Hexane → Ethyl alpha-nitro-9H-thioxanthene-9-acetate

HRID 2399625

反応式

HRID 2399625 の反応式
O[CH:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[N+:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:18])=[O:17].CCCCCC.[OH-].[K+]>O.C(O)C.CC(O)C>[N+:16]([CH:19]([CH:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:18])=[O:17]

参加物

8

反応物 4

HCID 8058HexaneHCID 14797Potassium HydroxideHCID 69379Ethyl nitroacetateHCID 51541709H-thioxanthen-9-ol

生成物 1

HCID 15290759Ethyl alpha-nitro-9H-thioxanthene-9-acetate

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒2 回HCID 962Water溶媒HCID 3776Isopropanol溶媒

反応条件

温度
100 °C

実験手順

Crude 9-hydroxythioxanthene (9.58 g, 45 mmol) is mixed with ethyl nitroacetate (5.5 mL, 49 mmol) and heated at 100° C. for 1 hour. TLC (SiO2, hexane:2-propanol/3:l) after 45 minutes shows no starting material. The cooled reaction mixture is treated with 100 mL of ethanol and 39 mL of 1.25M ethanolic potassium hydroxide solution. Ethanol is stripped and the residue taken up in water and extracted with diethyl ether. The aqueous layer is acidified to pH 2 to 3 with 85% phosphoric acid solution and refrigerated overnight. A crystalline solid is collected by filtration and dried at 50° C./10 mm Hg. A total of 8.4 g of the title compound is collected in three crops; mp 111°-115° C.

後処理

  1. customThe cooled reaction mixture
  2. extractionextracted with diethyl ether
  3. filtrationA crystalline solid is collected by filtration
  4. customdried at 50° C./10 mm Hg
  5. customA total of 8.4 g of the title compound is collected in three crops

出典と根拠

ORDレコード
ord-c65b29c2570c49998e2fdebbfdbf0651
出典データセット
uspto-grants-1995_09
特許番号
US05449778

関連ノート

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