Sodium hydride → HCID 13240321, compound

HRID 1649596Notes

Reaction equation

HRID 1649596 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[N:12][C:13](=[O:15])[CH:14]=1.[H][H].S(O[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36]([C:38]1[CH:39]([C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([N+:57]([O-:59])=[O:58])[CH:52]=2)[C:40]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[C:41]([CH3:45])[NH:42][C:43]=1[CH3:44])=[O:37])(C1C=CC(C)=CC=1)(=O)=O>CS(C)=O>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:11][N:12]=[C:13]([O:15][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36]([C:38]2[CH:39]([C:51]3[CH:56]=[CH:55][CH:54]=[C:53]([N+:57]([O-:59])=[O:58])[CH:52]=3)[C:40]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[C:41]([CH3:45])[NH:42][C:43]=2[CH3:44])=[O:37])[CH:14]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 20525506HCID 20525506, compoundHCID 86739135HCID 86739135, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13240321HCID 13240321, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

0.24 g (10 mmole) of sodium hydride was suspended in 10 ml of dimethylsulfoxide, to which was added gradually 1.95 g (10 mmole) of 3-o-chlorophenyl-5-pyrazolone with stirring at room temperature. After evolution of hydrogen had ceased, to this solution was added 10 ml of a solution of 6.01 g (10 mmole) of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3-ethoxycarbonylpyridine-5-carboxylic acid 6-tosyloxyhexyl ester in dimethylsulfoxide, and stirring with heating at 80° C. was continued for an hour. The resultant reaction mixture was poured into 150 ml of ice water, and the separated product was extracted with 50 ml of chloroform. This chloroform solution was washed with 50 ml of water 4 times, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a brown oily residue. This residue was purified by chromatography on a silica gel column using a mixed solution of chloroform-methanol (the ratio by volume of 100:1) as an eluent, and further by chromatography on a silica gel column eluting with a toluene-ethyl acetate mixed solution, and the eluate fractions containing the purified intended compound were concentrated to dryness under reduced pressure to obtain 2.55 g (yield 40.9%) of the 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3-ethoxycarbonylpyridine-5-carboxylic acid 6-(5-o-chlorophenyl-3-pyrazolyloxy)hexyl ester as a pale yellow powder.

Workup

  1. stirringstirring
  2. temperaturewith heating at 80° C.
  3. waitwas continued for an hour
  4. customThe resultant reaction mixture
  5. extractionthe separated product was extracted with 50 ml of chloroform
  6. washThis chloroform solution was washed with 50 ml of water 4 times
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain a brown oily residue
  10. customThis residue was purified by chromatography on a silica gel column
  11. washfurther by chromatography on a silica gel column eluting with a toluene-ethyl acetate mixed solution
  12. additionthe eluate fractions containing the purified intended compound
  13. concentrationwere concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-81c77cad02f847318fdd8b7aa53399ad
Source dataset
uspto-grants-1983_11
Patent number
US04418197

Reaction notes

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