2-Mercaptoethanol → HCID 54185176, compound

HRID 1514753Notes

Reaction equation

HRID 1514753 reaction equation
C(=O)([O-])[O-].[K+].[K+].[SH:7][CH2:8][CH2:9][OH:10].F[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15]>C(#N)CC>[OH:10][CH2:9][CH2:8][S:7][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 54185176HCID 54185176, compound

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent3×

Conditions

Temperature
85 °C

Procedure

To a slurry of potassium carbonate (362 g, 2.62 moles) in propionitrile (1000 ml) under nitrogen, was added 2-mercaptoethanol (184 ml, 2.618 moles) as a solution in propionitrile (750 ml). 2-Fluorobenzaldehyde (250 g, 2.014 moles) was added as a solution in propionitrile (750 ml) and heated at 85° C. for 18 hours. The reaction was cooled to 20° C. and sequentially washed with water (1500 ml), 1M sodium hydroxide solution (500 ml) and water (1000 ml). The final solution was dried by azeotropic distillation to leave the title compound as a clear, yellow solution in propionitrile (4250 ml). A small sample was concentrated for yield calculation (348.7 g, 95%).

Workup

  1. temperatureThe reaction was cooled to 20° C.
  2. washsequentially washed with water (1500 ml), 1M sodium hydroxide solution (500 ml) and water (1000 ml)
  3. dry with materialThe final solution was dried by azeotropic distillation

Sources & evidence

ORD record
ord-29e6d983412c4c06951d42067dd26713
Source dataset
uspto-grants-2012_07
Patent number
US08222273B2

Reaction notes

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