Oxalic Acid → HCID 3076419, compound

HRID 1494414Notes

Reaction equation

HRID 1494414 reaction equation
[NH:1]=[C:2]1[N:6]([CH2:7][CH2:8][S:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:5]2[CH:16]=[CH:17][C:18]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:19][C:4]=2[S:3]1.ClC1C=CC=C(C(OO)=[O:33])C=1.C(O)(=O)C(O)=O.C([O-])(=O)C([O-])=O>O.O1CCOCC1.CC(C)=O>[NH:1]=[C:2]1[N:6]([CH2:7][CH2:8][S:9]([C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)=[O:33])[C:5]2[CH:16]=[CH:17][C:18]([O:20][C:21]([F:23])([F:22])[F:24])=[CH:19][C:4]=2[S:3]1

Participants

8

Reactant 4

HCID 971Oxalic AcidHCID 70297m-Chloroperbenzoic acidHCID 71081OxalateHCID 3076386HCID 3076386, compound

Product 1

HCID 3076419HCID 3076419, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The procedure is as in Example 8, starting with 2-imino-3-[2-(4-pyridylthio)ethyl]-6-trifluoromethoxybenzothiazoline (2 g) and meta-chloroperbenzoic acid (90 pure by weight) (0.68 g) dissolved in water (25 cc) and dioxane (25 cc). The reaction mixture is stirred for 12 hours at 25.C and then concentrated to dryness at 40.C under reduced pressure (20 mm Hg; 2.7 KPa) to remove the dioxane. The aqueous solution is taken to a pH of 12-13 with concentrated ammonia solution (l0N) and then extracted with dichloromethane (2×50 cc). The organic phase is dried over anhydrous magnesium sulphate and concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The oil thereby obtained is purified by flash chromatography on a silica column under a stream of nitrogen at moderate pressure (0.5-1.5 bars), with a mixture of ethyl acetate and methanol (90:10 by volume) as eluent. An oil is thereby isolated, which oil, when treated with oxalic acid (0.25 g) and acetone (5 cc), gives 2-imino-3-[2-(4-pyridylsulphinyl)ethyl]-6trifluoromethoxybenzothiazoline (0.9 g) directly in the form of an oxalate, m.p. 194° C.

Workup

  1. concentrationconcentrated to dryness at 40.C under reduced pressure (20 mm Hg; 2.7 KPa)
  2. customto remove the dioxane
  3. extractionextracted with dichloromethane (2×50 cc)
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
  5. concentrationconcentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  6. customThe oil thereby obtained
  7. customis purified by flash chromatography on a silica column under a stream of nitrogen at moderate pressure (0.5-1.5 bars), with a mixture of ethyl acetate and methanol (90:10 by volume) as eluent
  8. customAn oil is thereby isolated

Sources & evidence

ORD record
ord-e0c0ab95c245418e930e21bac4c31373
Source dataset
uspto-grants-1991_06
Patent number
US05026717

Reaction notes

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