Methanol → 2-Imino-3-{2-[4-(2-methylphenyl)-1-piperazinyl]ethyl}-6-trifluoromethoxybenzothiazoline

HRID 256822

反応式

HRID 256822 の反応式
CS(O[CH2:6][CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:16][C:11]=2[S:10][C:9]1=[N:22]C(=O)C(F)(F)F)(=O)=O.[CH3:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.CO.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[NH:22]=[C:9]1[N:8]([CH2:7][CH2:6][N:39]2[CH2:40][CH2:41][N:36]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[CH3:29])[CH2:37][CH2:38]2)[C:12]2[CH:13]=[CH:14][C:15]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:16][C:11]=2[S:10]1

参加物

6

反応物 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 919652-MeppHCID 157348642-(2-Trifluoroacetylimino-6-trifluoromethoxy-3-benzothiazolinyl)ethyl methanesulphonate

生成物 1

HCID 157348672-Imino-3-{2-[4-(2-methylphenyl)-1-piperazinyl]ethyl}-6-trifluoromethoxybenzothiazoline収率 31.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
20 °C

実験手順

Using the procedure described in Example 1, starting with 2-(2-trifluoroacetylimino-6-trifluoromethoxy-3-benzothiazolinyl)ethyl methanesulphonate (5.88 g) in toluene (200 cc) and 4-(2-methylphenyl)piperazine (6.87 g) and after 2 hours under reflux, the toluene filtrate is evaporated under reduced pressure. To the residue thereby obtained, methanol (100 cc) and a 7% strength aqueous-alcoholic solution (20 cc) of potassium carbonate are added and the mixture is stirred for 2 hours at approximately 20° C. The alcohol is evaporated off under reduced pressure and the residue is purified by chromatography on a silica column with a dichloromethane/ethyl acetate mixture (70:30 by volume) as eluent, and then an ethyl acetate/cyclohexane mixture (50:50 by volume) as eluent. 2-Imino-3-{2-[4-(2-methylphenyl)-1-piperazinyl]ethyl}-6-trifluoromethoxybenzothiazoline (1.8 g), m.p. 135° C., is thereby obtained.

後処理

  1. temperatureunder reflux
  2. customthe toluene filtrate is evaporated under reduced pressure
  3. customTo the residue thereby obtained
  4. customThe alcohol is evaporated off under reduced pressure
  5. customthe residue is purified by chromatography on a silica column with a dichloromethane/ethyl acetate mixture (70:30 by volume) as eluent

出典と根拠

ORDレコード
ord-dc629171cd6642ad9df22a945bf19afc
出典データセット
uspto-grants-1993_11
特許番号
US05260297

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