Isopropanol → (RS)-3-(2-Dimethylaminopropyl)2-imino-6-trifluoromethoxybenzothiazoline

HRID 1494407노트

반응식

HRID 1494407 반응식
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.Cl[CH:18](C)[CH2:19][N:20]([CH3:22])[CH3:21].[CH3:24]C(O)C>>[CH3:21][N:20]([CH3:22])[CH:19]([CH3:24])[CH2:18][N:6]1[C:5]2[CH:7]=[CH:8][C:9]([O:11][C:12]([F:15])([F:13])[F:14])=[CH:10][C:4]=2[S:3][C:2]1=[NH:1]

참가 물질

4

반응물 3

HCID 3776IsopropanolHCID 5070RiluzoleHCID 942942-Chloropropyldimethylamine hydrochloride

생성물 1

HCID 3076394(RS)-3-(2-Dimethylaminopropyl)2-imino-6-trifluoromethoxybenzothiazoline

실험 절차

2-Amino-6-trifluoromethoxybenzothiazole (9.4 g) and 2-chloro-1-dimethylaminopropane hydrochloride (7.0 g) are heated for 1 hour to 130.C. 2-Propanol (20 cc) is added and heating is continued for 24 hours to boiling. After cooling of the mixture to a temperature in the region of 20.C, the precipitate is filtered off and then treated with IN sodium hydroxide (80 cc) in distilled water (100 cc). The residue obtained by extraction with dichloromethane, drying over magnesium sulphate and concentration to dryness under reduced pressure (20 mm Hg; 2.7 kPa) is purified by chromatography on a silica column with a mixture of ethyl acetate and methanol (80:20 by volume) as eluent. (RS)-3-(2-Dimethylaminopropyl)2-imino-6-trifluoromethoxybenzothiazoline (3.3 g) is obtained in the form of a yellow oil, which is converted to a dihydrochloride subliming at about 190° C.

후처리

  1. temperatureheating
  2. filtrationthe precipitate is filtered off
  3. additiontreated with IN sodium hydroxide (80 cc) in distilled water (100 cc)
  4. customThe residue obtained by extraction with dichloromethane
  5. dry with materialdrying over magnesium sulphate and concentration to dryness under reduced pressure (20 mm Hg; 2.7 kPa)
  6. customis purified by chromatography on a silica column with a mixture of ethyl acetate and methanol (80:20 by volume) as eluent

출처 및 근거

ORD 기록
ord-a1a7b94c320d4280a5278aaecd1f3e22
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05026717

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