Pyridine → HCID 19002334, compound

HRID 1742887Notes

Reaction equation

HRID 1742887 reaction equation
[C:1]([C:4]1[CH:8]=[N:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:5]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)(O)=[O:2].S(Cl)(Cl)=O.[CH3:30][NH:31][CH2:32][CH3:33].N1C=CC=CC=1>ClCCl.O>[CH3:30][N:31]([CH2:32][CH3:33])[C:1]([C:4]1[CH:8]=[N:7][N:6]([C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[C:5]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)=[O:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 12219N-MethylethylamineHCID 24386Thionyl ChlorideHCID 19002373HCID 19002373, compound

Product 1

HCID 19002334HCID 19002334, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
3 °C

Procedure

The acid prepared in Example 610 (2.6 g) is heated with 75% strength thionyl chloride (50 ml) for 8 hours. The mixture is taken up in dichloromethane and concentrated. The oil obtained (1.4 g) is dissolved in methylene chloride (30 ml) and cooled to about 3° C. A solution of N-methyl-N-ethylamine (0.54 g) and pyridine (0.3 g) in methylene chloride (30 ml) is added, keeping the temperature lower than 5° C. The mixture is stirred for 6 hours 20 minutes at ambient temperature. It is poured into water and extracted with methylene chloride. The mixture is dried over sodium sulphate and concentrated. An orange precipitate (1.2 g; yield=82.2%) is obtained, m.p. 110° C. (compound no. 611).

Workup

  1. concentrationconcentrated
  2. customThe oil obtained (1.4 g)
  3. customlower than 5° C
  4. extractionextracted with methylene chloride
  5. dry with materialThe mixture is dried over sodium sulphate
  6. concentrationconcentrated
  7. customAn orange precipitate (1.2 g; yield=82.2%) is obtained

Sources & evidence

ORD record
ord-9a6492235d214d50bac8df9f70a8e8e2
Source dataset
uspto-grants-1994_08
Patent number
US05342835

Reaction notes

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