Water → HCID 13245578, compound

HRID 904763Notes

Reaction equation

HRID 904763 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]([C:11]1[CH:12]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[C:13]([C:19]([O:21][CH3:22])=[O:20])=[C:14]([CH3:18])[NH:15][C:16]=1[CH3:17])=[O:10].[S:32](Cl)([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33].N1C=CC=CC=1.O>C(Cl)(Cl)Cl>[S:32]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]([C:11]1[CH:12]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[C:13]([C:19]([O:21][CH3:22])=[O:20])=[C:14]([CH3:18])[NH:15][C:16]=1[CH3:17])=[O:10])([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 13245577HCID 13245577, compound

Product 1

HCID 13245578HCID 13245578, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

43.3 g (0.10 mole) of the 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 3-methyl ester 5-(6-hydroxyhexyl) ester produced in Step i described above was dissolved along with 29.5 g (0.16 mole) of tosyl chloride in 200 ml of chloroform, to which was added dropwise 25.0 g (0.32 mole) of pyridine with stirring under ice cooling. This reaction mixture was allowed to stand at room temperature for 2 hours, then, after adding 100 ml of water, was stirred for 3 hours. The chloroform layer of the obtained liquid was separated, washed with 200 ml of 0.02 N sulfuric acid, 200 ml of water and 200 ml of saturated aqueous sodium bicarbonate successively, and dried over anhydrous sodium sulfate. This chloroform solution was chromatographed on a silica gel column using a mixed solution of benzene-ethyl acetate (the ratio by volume of 8:1) as an eluent to obtain 36.6 g (yield 62.5%) of the 1,4-dihydro- 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 3-methyl ester 5-(6-tosyloxyhexyl) ester as a pale yellow oil.

Workup

  1. stirringwas stirred for 3 hours
  2. customThe chloroform layer of the obtained liquid was separated
  3. washwashed with 200 ml of 0.02 N sulfuric acid, 200 ml of water and 200 ml of saturated aqueous sodium bicarbonate successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThis chloroform solution was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-226d6444992b4556965697335d3fed06
Source dataset
uspto-grants-1983_12
Patent number
US04419518

Reaction notes

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