Hydrochloric Acid → 2-Chlorophenyl-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetamide

HRID 598049Notes

Reaction equation

HRID 598049 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:11]1[CH2:16][CH2:15][C:14]2[S:17][CH:18]=[CH:19][C:13]=2[CH2:12]1)[C:9]#[N:10].C(=O)([O-])[O-:21].[K+].[K+].CS(C)=O.OO.Cl>O.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:11]1[CH2:16][CH2:15][C:14]2[S:17][CH:18]=[CH:19][C:13]=2[CH2:12]1)[C:9]([NH2:10])=[O:21]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 11369741rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile

Product 1

HCID 113128242-Chlorophenyl-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

(±)-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetonitrile (713 g; 2.46 mol) was added to methanol (3.505 l) at 23-28° C. with stirring. To this slurry, potassium carbonate (170 g; 1.23 mol) was added followed by dimethyl sulfoxide (263 ml; 3.7 mol). The contents were heated between 30-40° C. and 30.0% aqueous hydrogen peroxide solution (382 ml; 3.70 mol) was added between 40-50° C. slowly over a period of 3 hours. After the addition was over, the reaction mixture was maintained at this temperature for a further 2 hours, after which the reaction was brought to 20-30° C. 35% Hydrochloric acid (213.0 ml) in water (10.7 l) was added slowly to the reaction mixture over a period of 1 hour 15 minutes. After stirring for 1 hour, the solid formed was filtered and washed with a 1:1 methanol: water mixture (3.565 l). The isolated solid was dried in a vacuum oven at 75-80° C. for a period of 12 hours. Yield: 716 g (94.72%). mp: 124-126° C. The product was identified by IR spectrum, 1H and 13C NMR investigation.

Workup

  1. additionAfter the addition
  2. temperaturewas maintained at this temperature for a further 2 hours
  3. customwas brought to 20-30° C
  4. stirringAfter stirring for 1 hour
  5. customthe solid formed
  6. filtrationwas filtered
  7. washwashed with a 1:1 methanol
  8. customThe isolated solid was dried in a vacuum oven at 75-80° C. for a period of 12 hours

Sources & evidence

ORD record
ord-892dd5e36c7046ea9beab4616f63f829
Source dataset
uspto-grants-2011_03
Patent number
US07897613B2

Reaction notes

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