Hydrochloric Acid → HCID 18988358, compound

HRID 2396071Notes

Reaction equation

HRID 2396071 reaction equation
CO[C:3]1[CH:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7]3[CH:13]=[CH:14][CH2:15][S:16][C:6]=3[C:5]=2[CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:21]([SH:23])[CH3:22].Cl>C(Cl)Cl>[CH2:21]([S:23][C:3]1[CH:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7]3[CH:13]=[CH:14][CH2:15][S:16][C:6]=3[C:5]=2[CH:4]=1)[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343Ethanethiol2×HCID 6451240Aluminum(III) Chloride2×HCID 18988354HCID 18988354, compound

Product 1

HCID 18988358HCID 18988358, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

500 mg (1.9 mmol) of the compound obtained in Example 24, predissolved in 5cm3 of methylene chloride distilled over phosphorus pentoxide are added dropwise to a mixture, cooled to 0° C., of 380 mg (2.84 mmol)of aluminum chloride and 2.3 g (37.9 mmol) of ethanethiol. After stirring at 0° C. for 1 h, 1.5 eq. of aluminum chloride and 20 eq. of ethanethiol are added again. The mixture is stirred again for 1 h at 0° C. and then poured onto ice, treated with 1N hydrochloric acid and then extracted with dichloromethane. After treatment of the organic phase and purification of the crude product by chromatography on a silica column the expected compound is obtained.

Workup

  1. distillationdistilled over phosphorus pentoxide
  2. additionare added dropwise to a mixture
  3. stirringThe mixture is stirred again for 1 h at 0° C.
  4. additionpoured onto ice
  5. extractionextracted with dichloromethane
  6. customAfter treatment of the organic phase and purification of the crude product by chromatography on a silica column the expected compound
  7. customis obtained

Sources & evidence

ORD record
ord-bd3cd8c70b56413d947df2f7f6d48eb7
Source dataset
uspto-grants-1996_02
Patent number
US05491163

Reaction notes

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