HCID 19784284, compound → HCID 19784266, compound

HRID 256823Notes

Reaction equation

HRID 256823 reaction equation
[ClH:1].[C:2]1([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:21]4[CH:22]=[CH:23][C:24]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:25][C:20]=4[S:19][C:18]3=[N:31]C(=O)C(F)(F)F)[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(=O)([O-])[O-].[K+].[K+].CO>[ClH:1].[ClH:1].[NH:31]=[C:18]1[N:17]([CH2:16][CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:12]2)[C:21]2[CH:22]=[CH:23][C:24]([O:26][C:27]([F:28])([F:30])[F:29])=[CH:25][C:20]=2[S:19]1

Participants

4

Reactant 1

HCID 19784284HCID 19784284, compound

Product 1

HCID 19784266HCID 19784266, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
20 °C

Procedure

3-[3-(4-Phenyl-1-piperazinyl)propyl]-2-trifluoroacetylimino-6-trifluoromethoxybenzothiazoline hydrochloride (3.6 g), dissolved in a mixture of 7% strength aqueous potassium carbonate solution (45 cc) and methanol (150 cc), is stirred for 4 hours at a temperature in the region of 20° C. After concentration to dryness, the reaction medium is taken up in distilled water (100 cc) and the organic phase extracted with ethyl acetate (2×100 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (20 mmHg; 2.7 kPa). After formation of the dihydrochloride by adding 4.2N ethereal hydrogen chloride (4 cc) in ethyl acetate, the precipitate is recrystallized in an absolute ethanol/ethyl ether mixture (50:50 by volume). 2-Imino-3-[3-(4-phenyl-1-piperazinyl)propyl]-6-trifluoromethoxybenzothiazoline dihydrochloride (1.6 g), m.p. 260° C., is obtained.

Workup

  1. concentrationAfter concentration to dryness
  2. extractionthe organic phase extracted with ethyl acetate (2×100 cc)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (20 mmHg; 2.7 kPa)
  5. additionAfter formation of the dihydrochloride by adding 4.2N ethereal hydrogen chloride (4 cc) in ethyl acetate
  6. customthe precipitate is recrystallized in an absolute ethanol/ethyl ether mixture (50:50 by volume)

Sources & evidence

ORD record
ord-61d5359b527d4aaaa3e8057f3e57dc5b
Source dataset
uspto-grants-1993_11
Patent number
US05260297

Reaction notes

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