Sodium methanethiolate → 2(3H)-Benzothiazolimine, 3-[3-(methylthio)propyl]-6-(trifluoromethoxy)-

HRID 2255454Notes

Reaction equation

HRID 2255454 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][N:14]2[C:18]3[CH:19]=[CH:20][C:21]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:22][C:17]=3[S:16][C:15]2=[N:28]C(=O)C(F)(F)F)(=O)=O)=CC=1.[CH3:36][S-:37].[Na+]>C(O)C>[NH:28]=[C:15]1[N:14]([CH2:13][CH2:12][CH2:11][S:37][CH3:36])[C:18]2[CH:19]=[CH:20][C:21]([O:23][C:24]([F:25])([F:26])[F:27])=[CH:22][C:17]=2[S:16]1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 10674047HCID 10674047, compound

Product 1

HCID 105438302(3H)-Benzothiazolimine, 3-[3-(methylthio)propyl]-6-(trifluoromethoxy)-Yield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(2-Trifluoroacetylimino-6-trifluoromethoxy-3-benzothiazolinyl)propyl p-toluenesulphonate (3.88 g) and sodium methanethiolate (1.03 g) in absolute ethanol (20 cc) are heated at 60° C. for 6 hours. After cooling to a temperature close to 20° C., the reaction mixture is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa). The oily residue is taken up in distilled water (50 cc) and the organic phase is extracted with ethyl ether (50 cc). After drying over magnesium sulphate and concentrating to dryness under reduced pressure, 2-imino-3-(3-methylthiopropyl)-6-trifluoromethoxybenzothiazoline (1.88 g) is obtained, which is converted to the hydrochloride melting at 181° C.

Workup

  1. temperatureAfter cooling to a temperature
  2. customclose to 20° C.
  3. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa)
  4. extractionthe organic phase is extracted with ethyl ether (50 cc)
  5. dry with materialAfter drying over magnesium sulphate
  6. concentrationconcentrating to dryness under reduced pressure

Sources & evidence

ORD record
ord-750141a3ed3446e8aac3448cb479c759
Source dataset
uspto-grants-1993_08
Patent number
US05240948

Reaction notes

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