Ethanol → HCID 19856768, compound

HRID 365095Notes

Reaction equation

HRID 365095 reaction equation
[S:1]1C=CC=[C:2]1CC(O)=O.[C:10](=[O:13])([O-])[O-].[K+].[K+].C(O)C.Br[CH2:20][CH2:21][CH2:22][C:23]#[N:24]>O>[SH:1][CH2:2][C:10]([CH2:20][CH2:21][CH2:22][C:23]#[N:24])=[O:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 159702-Thiopheneacetic acidHCID 214124-Bromobutyronitrile

Product 1

HCID 19856768HCID 19856768, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Thiolacetic acid (49 mL, 0.69 mol) is added to potassium carbonate (93.4 g, 0.68 mol) dissolved in water (150 mL). Ethanol (260 mL) is added and then 4-bromobutyronitrile is added at 15° to 28° C. and the reaction mixture stirred at room temperature for 16 hours. The resulting inorganic solids are filtered off and the filtrate extracted with toluene. The organic layer is separated, dried over anhydrous Na2SO4 and concentrated to give the desired 4-mercaptoacetyl butyronitrile as a yellow oil.

Workup

  1. filtrationThe resulting inorganic solids are filtered off
  2. extractionthe filtrate extracted with toluene
  3. customThe organic layer is separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8b380ad0ac464789b6dd0cbc82cfda9c
Source dataset
uspto-grants-1986_08
Patent number
US04608079

Reaction notes

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