Hydrochloric Acid → HCID 20061605, compound

HRID 1085124Notes

Reaction equation

HRID 1085124 reaction equation
[Cl:1]C1C=CC=C(C(OO)=[O:9])C=1.[NH:12]=[C:13]1[N:17]([CH2:18][CH2:19][S:20][CH2:21][CH2:22][CH3:23])[C:16]2[CH:24]=[CH:25][C:26]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:27][C:15]=2[S:14]1.C(OCC)C.Cl>C(O)C>[ClH:1].[NH:12]=[C:13]1[N:17]([CH2:18][CH2:19][S:20]([CH2:21][CH2:22][CH3:23])=[O:9])[C:16]2[CH:24]=[CH:25][C:26]([O:28][C:29]([F:31])([F:32])[F:30])=[CH:27][C:15]=2[S:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 20061594HCID 20061594, compound

Product 1

HCID 20061605HCID 20061605, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-35 °C

Procedure

70-75% pure m-chloroperbenzoic acid (4.3 g) is added in the course of approximately 10 minutes to 2-imino-3-(2-propylthioethyl)-6-trifluoromethoxybenzothiazoline (5.87 g) dissolved in absolute ethanol (80 cc) cooled to -35° C. The reaction is continued for 10 minutes at the same temperature. The reaction medium is then added to ethyl ether (300 cc) and treated with 4.2N ethereal hydrogen chloride (4.2 cc). The precipitate formed is filtered off, then taken up in distilled water (50 cc) and neutralized with 1N sodium hydroxide. After extraction with ethyl acetate, drying over magnesium sulphate and concentration to dryness under reduced pressure (20 mm Hg; 2.7 kPa), the crude product is purified by chromatography on a silica column, with ethyl acetate and then a mixture of ethyl acetate and methanol (90:10 by volume) as eluents. After conversion to hydrochlorides, 2-imino-3-(2-propylsulphonylethyl)-6-trifluoromethoxybenzothiazoline hydrochloride (0.33 g), subliming at about 200° C., and (RS)-2-imino-3-(2-propylsulphinylethyl)-6-trifluoromethoxybenzothiazoline hydrochloride (2.63 g), m.p. 125° C., are obtained.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. extractionAfter extraction with ethyl acetate
  4. dry with materialdrying over magnesium sulphate and concentration to dryness under reduced pressure (20 mm Hg; 2.7 kPa)
  5. customthe crude product is purified by chromatography on a silica column, with ethyl acetate
  6. additiona mixture of ethyl acetate and methanol (90:10 by volume) as eluents
  7. customsubliming at about 200° C.

Sources & evidence

ORD record
ord-c8c26b5d102543ceba299644288fad6e
Source dataset
uspto-grants-1991_04
Patent number
US05008280

Reaction notes

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