Oxalic Acid → HCID 3076377, compound

HRID 1494404Notes

Reaction equation

HRID 1494404 reaction equation
BrBr.[F:3][C:4]([F:18])([F:17])[O:5][C:6]1[CH:16]=[CH:15][C:9]([NH:10][CH2:11][CH2:12][C:13]#[N:14])=[CH:8][CH:7]=1.[S-:19][C:20]#[N:21].[K+].[OH-].[Na+].C(O)(=O)C(O)=O>C(O)(=O)C.CC(C)=O.O>[NH:21]=[C:20]1[N:10]([CH2:11][CH2:12][C:13]#[N:14])[C:9]2[CH:8]=[CH:7][C:6]([O:5][C:4]([F:17])([F:18])[F:3])=[CH:16][C:15]=2[S:19]1

Participants

9

Reactant 5

HCID 971Oxalic AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 516872Potassium thiocyanateHCID 14836843HCID 14836843, compound

Product 1

HCID 3076377HCID 3076377, compoundYield 146.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Bromine (3.2 g; 1 cc) is added at room temperature to 3-(4-trifluoromethoxyanilino)propionitrile (3 g) and potassium thiocyanate (7.8 g) dissolved in acetic acid (50 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 by adding 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 evaporation to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa), a brown oil is isolated. This oil is dissolved in acetone (100 cc) and oxalic acid (2 g) is added. 2-Imino-3-(2-cyanoethyl)-6-trifluoromethoxy-benzothiazoline (5.5 g) is thereby isolated in the form of a monooxylate, m.p. 180° 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 and evaporation to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  7. customa brown oil is isolated

Sources & evidence

ORD record
ord-9c30407fe6d9482ab96558ba3d9ab94d
Source dataset
uspto-grants-1991_06
Patent number
US05026717

Reaction notes

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