Ethanethiol → HCID 86737097, compound

HRID 2057868Notes

Reaction equation

HRID 2057868 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=[C:3]1[CH2:16][C:17]#N.[CH2:19]([SH:21])[CH3:20].[CH2:22]1[CH2:26][O:25][CH2:24][CH2:23]1>>[CH2:16]([C:3]1[N:2]([CH3:1])[C:6]([C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[O:8])=[CH:5][CH:4]=1)[CH3:17].[S:21]1[CH:19]=[CH:20][CH:26]=[C:22]1[CH2:23][C:24]([O-:8])=[O:25]

Participants

4

Reactant 3

HCID 6343EthanethiolHCID 8028TetrahydrofuranHCID 111074051-Methyl-5-(p-toluoyl)pyrrole-2-acetonitrile

Product 1

HCID 86737097HCID 86737097, compoundYield 42.5%

Conditions

Temperature
-20 °C

Procedure

To a dry 100 ml three-necked flask under nitrogen is added 1-methyl-5-(p-toluoyl)pyrrole-2-acetonitrile (4.0 g, 0.0168 mole) and 30 ml of dry THF. The solution is cooled to -20° C., ethyl mercaptan (1.38 ml, 0.0180 mole) is added and hydrogen chloride is then bubbled into the reaction mixture. When the reaction mixture is saturated with HCl the temperature is raised to and maintained at 0° C. for 2.5 hrs. The reaction mixture is poured into a three-necked, 300 ml round-bottom flask, 100 ml of toluene is added and steam blown into the organic layer until the red color disappears. The toluene layer is separated and the water layer washed twice with toluene. The toluene extracts are combined, washed with brine and dried over anhydrous MgSO4. The solvent is evaporated in vacuo to yield 4.27 g (84.4%) of crude product. One recrystallization from methanol yields 2.15 g (42.5%) of ethyl 1-methyl-5-(p-toluoyl)-pyrrole-2-thiolacetate, m.p. 74° -76° C.

Workup

  1. customhydrogen chloride is then bubbled into the reaction mixture
  2. temperatureis raised to and
  3. temperaturemaintained at 0° C. for 2.5 hrs
  4. additionThe reaction mixture is poured into a three-necked, 300 ml round-bottom flask
  5. addition100 ml of toluene is added
  6. customThe toluene layer is separated
  7. washthe water layer washed twice with toluene
  8. washwashed with brine
  9. dry with materialdried over anhydrous MgSO4
  10. customThe solvent is evaporated in vacuo
  11. customto yield 4.27 g (84.4%) of crude product
  12. customOne recrystallization from methanol

Sources & evidence

ORD record
ord-fe300efa0e9a45a69c329300f6a649e9
Source dataset
uspto-grants-1980_07
Patent number
US04213905

Reaction notes

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