Acetyl chloride → 5-Acetyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxaldehyde

HRID 2216620Notes

Reaction equation

HRID 2216620 reaction equation
Cl.[S:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[C:3]1[CH:11]=[O:12].[C:13](Cl)(=[O:15])[CH3:14]>C(Cl)Cl>[C:13]([N:7]1[CH2:8][CH2:9][C:10]2[S:2][C:3]([CH:11]=[O:12])=[CH:4][C:5]=2[CH2:6]1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 11845087HCID 11845087, compound

Product 1

HCID 219414645-Acetyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxaldehydeYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold (0° C.) suspension of 1.5 g.(7.4 mmol) of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carbaldehyde hydrochloride in 50 mL methylene chloride, under N2 atm., dry conditions, was added dropwise under stirring 2.6 mL (2.5 eqs) of triethylamine. RM stirred for 30 min at 0°C. and a solution of 0.7 g.(8.1 mmol,1.1 eqs) of acetyl chloride in 15 mL methylene chloride was dropwise added, RM allowed to reach RT and stirred for 3 hours. Filtered trough a celite pad, filtrate washed with 3×50 mL water, dried, evaporated, gave 1.1 g.(71.4%) of the title compound, viscous oil, (M+H)+210.3.

Workup

  1. additionTo a cold (0° C.) suspension of 1.5 g
  2. custom, dry conditions
  3. additionwas added dropwise
  4. stirringRM stirred for 30 min at 0°C.
  5. customto reach RT
  6. stirringstirred for 3 hours
  7. filtrationFiltered trough a celite pad, filtrate
  8. washwashed with 3×50 mL water
  9. customdried
  10. customevaporated
  11. customgave 1.1 g

Sources & evidence

ORD record
ord-a00034e1833e44e3a5878a98701b5acd
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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