m-Chloroperbenzoic acid → HCID 3076390, compound

HRID 1111363Notes

Reaction equation

HRID 1111363 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[NH:12]=[C:13]1[N:17]([CH2:18][CH2:19][S:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]2[CH:27]=[CH:28][C:29]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:30][C:15]=2[S:14]1>C(O)C>[NH:12]=[C:13]1[N:17]([CH2:18][CH2:19][S:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:9])[C:16]2[CH:27]=[CH:28][C:29]([O:31][C:32]([F:34])([F:35])[F:33])=[CH:30][C:15]=2[S:14]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 3076416HCID 3076416, compound

Product 1

HCID 3076390HCID 3076390, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

m-Chloroperbenzoic acid (0.6 g) is added in the course of approximately 10 minutes to 2-imino-3-(2-phenylthioethyl)-6-trifluoromethoxybenzothiazoline (1.3 g) in absolute ethanol (20 cc) cooled to 0° C. The reaction is continued for 3 hours at a temperature in the region of 20° C. The reaction medium is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) and the residue obtained purified by chromatography on a silica column with ethyl acetate as eluent. (RS)-2-Imino-3-(2-phenylsulphinylethyl)-6-trifluoromethoxybenzothiazoline (0.7 g) is obtained in the form of a yellowish oil, which is converted to a hydrochloride, m.p. 210° C.

Workup

  1. concentrationThe reaction medium is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa)
  2. customthe residue obtained
  3. custompurified by chromatography on a silica column with ethyl acetate as eluent

Sources & evidence

ORD record
ord-8e4a3d4d88bc4b4c8fb597ad1e39d264
Source dataset
uspto-grants-1990_12
Patent number
US04980356

Reaction notes

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