Diethyl Ether → 3-[2-(Phenylsulfanyl)ethyl]-6-(trifluoromethoxy)-1,3-benzothiazol-2(3H)-imine--hydrogen chloride (1/1)

HRID 1494413Notes

Reaction equation

HRID 1494413 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:16][CH2:17][CH2:18][S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[I-].[Na+].C(OCC)C>C(C(C)=O)C>[ClH:16].[NH:1]=[C:2]1[N:6]([CH2:17][CH2:18][S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]2[CH:7]=[CH:8][C:9]([O:11][C:12]([F:15])([F:13])[F:14])=[CH:10][C:4]=2[S:3]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 5070RiluzoleHCID 5238Sodium IodideHCID 21702((2-Chloroethyl)thio)benzene

Product 1

HCID 30764153-[2-(Phenylsulfanyl)ethyl]-6-(trifluoromethoxy)-1,3-benzothiazol-2(3H)-imine--hydrogen chloride (1/1)Yield 33.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
20 °C

Procedure

The procedure is as in Example 21, starting with 2-amino-6-trifluoromethoxybenzothiazole (9.4 g), 1-chloro-2phenylthioethane (13.8 g) and sodium iodide (13.5 g) in methyl ethyl ketone (30 cc). The mixture is heated for 88 hours to boiling and then cooled to a temperature in the region of 20° C. Ethyl ether (250 cc) is added to the reaction medium and the precipitate formed is filtered off. The solid is suspended in distilled water (250 cc), treated with 1N sodium hydroxide (40 cc) and then extracted with ethyl ether (100 cc). After drying over magnesium sulphate and filtration, ethyl acetate (150 cc) is added to the filtrate, which is treated with 4N ethereal hydrogen chloride (10 cc). The precipitate formed is filtered off and recrystallized in 2-propanol (85 cc). 2-Imino-3-(2-phenylthioethyl)-6- trifluoromethoxybenzothiazoline hydrochloride (5.4 g), m.p. 174° C., is obtained.

Workup

  1. temperatureThe mixture is heated for 88 hours
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. additiontreated with 1N sodium hydroxide (40 cc)
  5. extractionextracted with ethyl ether (100 cc)
  6. dry with materialAfter drying over magnesium sulphate and filtration, ethyl acetate (150 cc)
  7. additionis added to the filtrate, which
  8. additionis treated with 4N ethereal hydrogen chloride (10 cc)
  9. customThe precipitate formed
  10. filtrationis filtered off
  11. customrecrystallized in 2-propanol (85 cc)

Sources & evidence

ORD record
ord-3c18e9c9a7f241da97dfebef494fec33
Source dataset
uspto-grants-1991_06
Patent number
US05026717

Reaction notes

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