Sodium Chloride → 2,6-Dimethyl-3-carbotert.-butoxy-4-(2-nitrophenyl)-5-methylsulphonyl-1,4-dihydro pyridine

HRID 328577Notes

Reaction equation

HRID 328577 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[C:12]([O:16][C:17](=[O:22])/[CH:18]=[C:19](\[NH2:21])/[CH3:20])([CH3:15])([CH3:14])[CH3:13].[CH3:23][S:24]([CH2:27][C:28](=O)[CH3:29])(=[O:26])=[O:25].[Cl-].[Na+]>CN(C)P(=O)(N(C)C)N(C)C.C(OCC)(=O)C.CO.O>[CH3:20][C:19]1[NH:21][C:28]([CH3:29])=[C:27]([S:24]([CH3:23])(=[O:26])=[O:25])[CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])[C:18]=1[C:17]([O:16][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:22]

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 111012-NitrobenzaldehydeHCID 786951-(Methylsulphonyl)acetoneHCID 12221517HCID 12221517, compound

Product 1

HCID 214428912,6-Dimethyl-3-carbotert.-butoxy-4-(2-nitrophenyl)-5-methylsulphonyl-1,4-dihydro pyridine

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

4.5 g of o-nitrobenzaldehyde, 6.3 g of 3-aminocrotonic acid tert.-butyl ester and 4.1 g of methylsulphonylacetone are stirred in 30 ml of hexamethylphosphoric acid triamide for 8 hours under nitrogen at a bath temperature of 110° C. The mixture is cooled and dissolved in 200 ml of ethyl acetate and the solution is treated with a mixture of 200 ml of water, 30 ml of methanol and 30 ml of sodium chloride solution. The aqueous phase is separated off and the organic phase is washed three times with 50 ml of water, twice with 50 ml of 1 N hydrochloric acid, twice with 50 ml of sodium bicarbonate and once with 50 ml of 2 N sodium carbonate solution. The organic phase is separated off and dried. The residue is recrystallised from isopropanol. 2,6-Dimethyl-3-carbotert.-butoxy-4-(2-nitrophenyl)-5-methylsulphonyl-1,4-dihydro pyridine, which is thus obtained, melts at 152°-155° C.

Workup

  1. temperatureThe mixture is cooled
  2. customThe aqueous phase is separated off
  3. washthe organic phase is washed three times with 50 ml of water
  4. customThe organic phase is separated off
  5. customdried
  6. customThe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-07baa0f9762644088660a7a514e01739
Source dataset
uspto-grants-1977_04
Patent number
US04017629

Reaction notes

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