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

HRID 1494407ノート

反応式

HRID 1494407 の反応式
[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]

参加物

4

反応物 3

HCID 3776IsopropanolHCID 5070RiluzoleHCID 942942-Chloropropyldimethylamine hydrochloride

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a1a7b94c320d4280a5278aaecd1f3e22
出典データセット
uspto-grants-1991_06
特許番号
US05026717

反応ノート

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