Hydrochloric Acid → HCID 18988356, compound

HRID 2396070Notes

Reaction equation

HRID 2396070 reaction equation
CO[C:3]1[CH:11]=[C:10]2[C:6]([C:7]3[CH:16]([CH3:17])[CH2:15][CH2:14][CH2:13][CH2:12][C:8]=3[NH:9]2)=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:22]([SH:24])[CH3:23].Cl>C(Cl)Cl>[CH2:22]([S:24][C:3]1[CH:11]=[C:10]2[C:6]([C:7]3[CH:16]([CH3:17])[CH2:15][CH2:14][CH2:13][CH2:12][C:8]=3[NH:9]2)=[CH:5][CH:4]=1)[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343Ethanethiol2×HCID 6451240Aluminum(III) Chloride2×HCID 18988350HCID 18988350, compound

Product 1

HCID 18988356HCID 18988356, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

500 mg (1.9 mmol) of the compound obtained in Stage B of Example 1, predissolved in 5 cm3 of methylene chloride distilled over phosphoruspentoxide 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 for 1 h at 0° C., 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 asilica column, the expected compound is obtained.

Workup

  1. distillationdistilled over phosphoruspentoxide
  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 asilica column

Sources & evidence

ORD record
ord-460210082bfa47a2a980b0e31725cbca
Source dataset
uspto-grants-1996_02
Patent number
US05491163

Reaction notes

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