Pyridine → HCID 23568954, compound

HRID 2220316Notes

Reaction equation

HRID 2220316 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH:9]=[C:10]([C:12](O)=O)[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.CS(Cl)(=O)=O.[N:20]1C=CC=CC=1>>[CH3:1][O:2][C:3]1[C:8]2[CH:9]=[C:10]([C:12]#[N:20])[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chloride2×HCID 227216294-Methoxy-1-benzothiophene-2-carboxylic acid

Product 1

HCID 23568954HCID 23568954, compoundYield 74%

Procedure

(Ref: Cheutin et al.; C.R. Hebd. Seances Acad. Sci; 261; 1965; 705.) A solution of 4-methoxy-1-benzothiophene-2-carboxylic acid (1.19 g, 5.7 mmol) in pyridine (25 mL) at 0° C. was treated with methanesulfonyl chloride (0.49 mL, 6.3 mmol) keeping the temperature at 0° C., stirring was continued for 2 h. Ammonia gas was then bubbled through the mixture for 5 minutes, followed by nitrogen for 10 mins. The reaction mixture was then treated with a large excess of mesyl chloride (4.43 mL, 57 mmol) and stirred for 16 h at room temperature. The solvent evaporated in vacuo to give a brown residue which was purified by flash chromatography with 10% ethyl acetate in hexane to give a colourless solid (800 mg, 74%); δH (300 MHz, CDCl3) 8.00 (1H, s, 3-ArH), 7.48-7.35 (2H, m, ArH), 6.80-6.77 (1H, m, ArH) and 3.92 (3H, s, OCH3).

Workup

  1. customat 0° C.
  2. customAmmonia gas was then bubbled through the mixture for 5 minutes
  3. waitfollowed by nitrogen for 10 mins
  4. stirringstirred for 16 h at room temperature
  5. customThe solvent evaporated in vacuo
  6. customto give a brown residue which
  7. customwas purified by flash chromatography with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e0db16f14d05439aba1828ea58ebc1fe
Source dataset
uspto-grants-2008_08
Patent number
US07417064B2

Reaction notes

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