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

HRID 1769546

반응식

HRID 1769546 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매2회HCID 962Water용매HCID 3776Isopropanol용매

반응 조건

온도
100 °C

실험 절차

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/3:1) 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.

후처리

  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

출처 및 근거

ORD 기록
ord-f01a81cc0b12418786f7e3ff01829498
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380925

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