Isopropanol → alpha-Amino-9H-thioxanthene-9-acetic acid, hydrochloride

HRID 1769548노트

반응식

HRID 1769548 반응식
[ClH:1].[NH2:2][CH:3]([CH:9]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:4]([O:6]CC)=[O:5].[OH-].[K+].CCCCCC.CC(O)C>C(O)C.O>[ClH:1].[NH2:2][CH:3]([CH:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[S:16][C:17]2[C:22]1=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:4]([OH:6])=[O:5]

참가 물질

7

반응물 4

HCID 3776IsopropanolHCID 8058HexaneHCID 14797Potassium HydroxideHCID 67804420Ethyl alpha-amino-9H-thioxanthene-9-acetate hydrochloride

생성물 1

HCID 67803772alpha-Amino-9H-thioxanthene-9-acetic acid, hydrochloride수율 18.5%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

Ethyl α-amino-9H-thioxanthene-9-acetate hydrochloride (3.5 g, 10 mmol) is dissolved in 30 mL of absolute ethanol and 33 mL of 1.25M ethanolic potassium hydroxide solution (4 equivalents) is added. The reaction mixture is stirred at room temperature for 22 hours when TLC (SiO2, hexane: 2-propanol/3:1) shows no starting material. Ethanol is stripped under vacuum and the residue taken up in 75 mL of water and extracted with diethyl ether. The aqueous solution is acidified with 1N hydrochloric acid to pH 7 and a precipitate is collected by filtration, washed with water, dried at 45° C./2 mm Hg over phosphorous pentoxide (P2O5). This gives 1.65 g of the title compound; mp 244°-246° C. The mother liquor is concentrated, cooled at +3° C. to furnish the second crop (0.57 g) of the title compound as a hydrochloride-free base mixture. The above solids are combined in 50 mL of water and treated with 1N hydrochloric acid to pH 1. The mixture is stripped to dryness under vacuum and the residue dried at 50 ° C./2 mm Hg to give the title compound; mp 269°-273° C. (dec).

후처리

  1. extractionextracted with diethyl ether
  2. filtrationa precipitate is collected by filtration
  3. washwashed with water
  4. dry with materialdried at 45° C./2 mm Hg over phosphorous pentoxide (P2O5)
  5. concentrationThe mother liquor is concentrated
  6. temperaturecooled at +3° C.

출처 및 근거

ORD 기록
ord-9747773119704e49aa95f8738ec9fd1e
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380925

반응 노트

불러오는 중…