Sulfuric Acid → (+/-)-(2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetamide Hydrogen Sulfate Salt

HRID 988845Notes

Reaction equation

HRID 988845 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:12]1[CH2:17][CH2:16][C:15]2[S:18][CH:19]=[CH:20][C:14]=2[CH2:13]1)[C:9]([NH2:11])=[O:10].ClC1C=CC=CC=1C(N1CCC2SC=CC=2C1)C#N.[S:40](=[O:44])(=[O:43])([OH:42])[OH:41].C(OCC)C>CC(C)=O>[S:40]([OH:44])([OH:43])(=[O:42])=[O:41].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:12]1[CH2:17][CH2:16][C:15]2[S:18][CH:19]=[CH:20][C:14]=2[CH2:13]1)[C:9]([NH2:11])=[O:10]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 113128242-Chlorophenyl-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetamideHCID 11369741rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile

Product 1

HCID 86586489(+/-)-(2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetamide Hydrogen Sulfate SaltYield 76%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2 g (6.48 mole) of (±)-(2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetamide of formula (IV), was dissolved in 10 mL acetone. To the reaction mixture 1 mL of sulfuric acid was added and was stirred for 0.5 hr. Later 5 mL of diethyl ether was added and stirred overnight at room temperature to obtain a salt. The salt 2 g (76%) was isolated by filtration and washed with acetone.

Workup

  1. stirringstirred overnight at room temperature
  2. customto obtain a salt

Sources & evidence

ORD record
ord-53520a5eed82450c94808a347a3400f6
Source dataset
uspto-grants-2003_10
Patent number
US06635763B2

Reaction notes

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