m-Chloroperbenzoic acid → 3-[2-(Pyrimidine-2-sulfinyl)ethyl]-6-(trifluoromethoxy)-1,3-benzothiazol-2(3H)-imine

HRID 1111374Notes

Reaction equation

[NH:1]=[C:2]1[N:6]([CH2:7][CH2:8][S:9][C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N: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(Cl)(Cl)Cl>[NH:1]=[C:2]1[N:6]([CH2:7][CH2:8][S:9]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=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

Conditions

Temperature: 20 °C

Procedure

The procedure is as in Example 8, starting with 2-imino-3-[2-(2-pyrimidinylthio)ethyl]-6-trifluoromethoxybenzothiazoline (0.5 g) and meta-chloroperbenzoic acid (90% pure by weight) (1 g) dissolved in chloroform (20 cc). The reaction mixture is stirred for 1 hour at a temperature in the region of 20° C. and then concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue 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 (95:5 by volume) as eluent. 2-Imino-3-[2-(2-pyrimidinylsulphinyl)ethyl]-6-trifluoromethoxybenzothiazoline (0.35 g), m.p. 120° C., is isolated.

Workup

concentrationconcentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)
customThe residue 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 (95:5 by volume) as eluent

Sources & evidence

ORD record: ord-ea3d9001e82b4a9dbd31041fec8e0e2e
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04980356

Reaction notes

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