2-Chlorobenzaldehyde → rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile

HRID 988843Notes

Reaction equation

HRID 988843 reaction equation
S(=O)(O)[O-].[Na+].[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=O.[S:15]1[C:23]2[CH2:22][CH2:21][NH:20][CH2:19][C:18]=2[CH:17]=[CH:16]1.[C-:24]#[N:25].[Na+]>O>[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]([N:20]1[CH2:21][CH2:22][C:23]2[S:15][CH:16]=[CH:17][C:18]=2[CH2:19]1)[C:24]#[N:25]

Participants

6

Reactant 4

HCID 69962-ChlorobenzaldehydeHCID 8929Sodium CyanideHCID 30850764,5,6,7-Tetrahydrothieno(3,2-c)pyridineHCID 23665763Sodium Bisulfite

Product 1

HCID 11369741rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 8.98 g (86.33 mmole) sodium bisulfite in water (27 mL), o-chlorobenzaldehyde 12.4 g (86.33 mmole) was added resulting in a white precipitate. To the precipitate, 15 g (0.107 moles) of 6,7-dihydro-4H-thieno[3,2-c]pyridine was added, followed by addition of 4.4 g (89.7 mmoles) NaCN (dissolved in 15 mL water). The reaction mixture was heated at 40-50° C. for 6 hrs and was quenched by pouring in water (50 mL). The mixture was extracted with 2×100 mL of ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The yield of the title product is 24 g (97%).

Workup

  1. customresulting in a white precipitate
  2. customwas quenched
  3. additionby pouring in water (50 mL)
  4. extractionThe mixture was extracted with 2×100 mL of ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4def2b3fe70d4c5a8a38613c009e1ed8
Source dataset
uspto-grants-2003_10
Patent number
US06635763B2

Reaction notes

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