Hydrochloric Acid → HCID 14836862, compound

HRID 2254646Notes

Reaction equation

HRID 2254646 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:9]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:4]=1[NH2:5].[S-:16][C:17]#[N:18].[K+].[OH-].[Na+].Cl.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(O)(=O)C.BrBr.C(OCC)C.O>[CH3:1][N:2]([CH3:15])[C:3]1[C:4]2[N:5]=[C:17]([NH2:18])[S:16][C:6]=2[CH:7]=[C:8]([O:10][C:11]([F:12])([F:13])[F:14])[CH:9]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 516872Potassium thiocyanateHCID 19742934HCID 19742934, compound

Product 1

HCID 14836862HCID 14836862, compoundYield 27.8%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 24408BromineSolvent

Procedure

The procedure is as in Example 1, starting with 2-dimethylamino-4-trifluoromethoxyaniline (2 g), potassium thiocyanate (3.5 g) dissolved in acetic acid (30 cc) and bromine (1.45 g; 0.47 cc). Stirring is maintained for 12 hours at this temperature. The mixture is evaporated to dryness at 80° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue obtained is taken up with water (100 cc) and the pH is brought to 9-10 with concentrated sodium hydroxide (10N). After extraction with ethyl acetate (2×50 cc), washing of the combined phases with water (2×20 cc), drying over anhydrous magnesium sulphate and evaporating to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa), a brown oil is isolated, which oil is purified by flash chromatography on a column of silica under a stream of nitrogen at moderate pressure (0.5-1.5 bars), with a dichloromethane/methanol mixture (99:1 by volume). A solid is isolated, which is dissolved in ethyl ether (30 cc), and ethereal hydrogen chloride (6.2N) is added until precipitation is complete. 4-Dimethylamino-6-trifluoromethoxy-2-benzothiazolamine (0.7 g) is thereby isolated in the form of a dihydrochloride, m.p. 184° C.

Workup

  1. temperatureis maintained for 12 hours at this temperature
  2. customThe mixture is evaporated to dryness at 80° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  3. customThe residue obtained
  4. extractionAfter extraction with ethyl acetate (2×50 cc)
  5. washwashing of the combined phases with water (2×20 cc)
  6. dry with materialdrying over anhydrous magnesium sulphate
  7. customevaporating to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  8. customa brown oil is isolated
  9. customwhich oil is purified by flash chromatography on a column of silica under a stream of nitrogen at moderate pressure (0.5-1.5 bars), with a dichloromethane/methanol mixture (99:1 by volume)
  10. customA solid is isolated

Sources & evidence

ORD record
ord-8c313418eb3049b1bdc36e766db17a54
Source dataset
uspto-grants-1993_08
Patent number
US05236940

Reaction notes

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