Potassium Carbonate → 2-Imino-3-{2-[4-(4-methoxyphenyl)-1-piperazinyl]ethyl}-6-trifluoromethoxybenzothiazoline trihydrochloride

HRID 256825Notes

Reaction equation

HRID 256825 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]3[C:22]4[CH:23]=[CH:24][C:25]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:26][C:21]=4[S:20][C:19]3=[N:32]C(=O)C(F)(F)F)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[ClH:1].[ClH:1].[ClH:1].[NH:32]=[C:19]1[N:18]([CH2:17][CH2:16][N:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=3)[CH2:11][CH2:12]2)[C:22]2[CH:23]=[CH:24][C:25]([O:27][C:28]([F:29])([F:31])[F:30])=[CH:26][C:21]=2[S:20]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 197842683-{2-[4-(4-Methoxyphenyl)-1-piperazinyl]ethyl}-2-trifluoroacetylimino-6-trifluoromethoxybenzothiazoline hydrochloride

Product 1

HCID 197842642-Imino-3-{2-[4-(4-methoxyphenyl)-1-piperazinyl]ethyl}-6-trifluoromethoxybenzothiazoline trihydrochlorideYield 214.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

3-{2-[4-(4-Methoxyphenyl)-1-piperazinyl]ethyl}-2-trifluoroacetylimino-6-trifluoromethoxybenzothiazoline hydrochloride (1.53 g), methanol (33 cc) and 7% strength potassium carbonate solution (21 cc) in a mixture of methanol (2 volumes) and water (5 volumes) are stirred for 4 hours at a temperature in the region of 20° C. The reaction medium is concentrated under reduced pressure and then extracted with ethereal sulphuric acid. The organic phase is dried over magnesium sulphate and then treated with an excess of alcoholic hydrochloric acid solution. The precipitate is drained, washed with ethereal sulphuric acid and dried at 50° C. at 20 mmHg. 2-Imino-3-{2-[4-(4-methoxyphenyl)-1-piperazinyl]ethyl}-6-trifluoromethoxybenzothiazoline trihydrochloride (1.05 g), m.p. 240° C., is obtained.

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure
  2. extractionextracted with ethereal sulphuric acid
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. additiontreated with an excess of alcoholic hydrochloric acid solution
  5. washwashed with ethereal sulphuric acid
  6. customdried at 50° C. at 20 mmHg

Sources & evidence

ORD record
ord-e6ce4959ff8e42869a5c9e2d991ba811
Source dataset
uspto-grants-1993_11
Patent number
US05260297

Reaction notes

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