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

HRID 256822

Reaction equation

HRID 256822 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dc629171cd6642ad9df22a945bf19afc
Source dataset
uspto-grants-1993_11
Patent number
US05260297

Linked notes

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