Sodium Methoxide → 3-Amino-2-[2-(4-chlorophenylsulfonyl)-acetyl]-6-methyl-thieno[2,3-b]-pyridine

HRID 223594Notes

Reaction equation

HRID 223594 reaction equation
C[O-].[Na+].[SH:4][C:5]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]([CH3:13])[N:6]=1.Cl[CH2:15][C:16](=[O:28])[CH2:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>CO.O>[NH2:12][C:11]1[C:10]2[C:5](=[N:6][C:7]([CH3:13])=[CH:8][CH:9]=2)[S:4][C:15]=1[C:16](=[O:28])[CH2:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19]

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 155811721-Chloro-3-(4-chlorobenzene-1-sulfonyl)propan-2-oneHCID 178425618HCID 178425618, compound

Product 1

HCID 155811733-Amino-2-[2-(4-chlorophenylsulfonyl)-acetyl]-6-methyl-thieno[2,3-b]-pyridineYield 67.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 5.4 g (0.1 mol) of sodium methoxide and 7.5 g (0.05 mol) of 2-mercapto-3-cyano-6-methyl pyridine in 100 ml methanol was slowly added 13.3 g (0.05 mol) of 3-chloro-1-(4-chloro-phenylsulfonyl)-2-propanone. The reaction mixture was refluxed for 7 hours. It was then cooled, diluted with water and filtered to give 15.5 g of crude product which was crystallized from acetonitrile to give 12.8 g of pure product, m.p. 265°-7° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 7 hours
  2. temperatureIt was then cooled
  3. filtrationfiltered
  4. customto give 15.5 g of crude product which
  5. customwas crystallized from acetonitrile

Sources & evidence

ORD record
ord-96c2fdcf908f486da79cf2e56a390ad3
Source dataset
uspto-grants-1982_10
Patent number
US04355164

Reaction notes

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