Thionyl Chloride → HCID 22574076, compound

HRID 23400Notes

Reaction equation

HRID 23400 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]#[N:13])[CH:6]=[C:5]2[S:14]([CH3:16])=O.C(=O)(O)[O-].[Na+].S(Cl)([Cl:24])=O>C(Cl)Cl>[Cl:24][C:6]1[N:7]([CH2:11][C:12]#[N:13])[C:8]2[C:4]([C:5]=1[S:14][CH3:16])=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2

Participants

5

Reactant 3

HCID 24386Thionyl Chloride2×HCID 516892Sodium BicarbonateHCID 22574044(5-Chloro-3-methanesulfinyl-indol-1-yl)-acetonitrile

Product 1

HCID 22574076HCID 22574076, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Following a procedure similar to that reported by Greenhouse et al., J. Org. Chem. 53 (1988) 2634, a solution of (5-chloro-3-methanesulfinyl-indol-1-yl)-acetonitrile (0.851 g, 3.38 mmole) in methylene chloride (85 ml) was cooled to 0° C. and solid sodium bicarbonate (3.66 g) was added. Thionyl chloride (0.422 g, 3.55 mmole) was dissolved in methylene chloride and added dropwise over a 45 minute period. Upon termination of addition, the reaction mixture was stirred an additional 15 m. Tlc analysis revealed the presence of a small amount of starting material. Additional thionyl chloride was added, one drop at a time until tlc analysis revealed the total consumption of starting material. When no more starting material was present, the entire reaction mixture was poured onto a short silica gel column and the product was eluted with methylene chloride and isolated by evaporation of the solvent to afford 0.657 g (72%) pure (2,5-dichloro-3-methylsulfanyl-indol-1-yl)-acetonitrile.

Workup

  1. additionadded dropwise over a 45 minute period
  2. additionUpon termination of addition
  3. customthe total consumption of starting material
  4. customthe entire reaction mixture
  5. additionwas poured onto a short silica gel column
  6. washthe product was eluted with methylene chloride
  7. customisolated by evaporation of the solvent

Sources & evidence

ORD record
ord-b0a8cb39738a4fc0b1a4cd3eda7343c9
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

Loading…