Sodium Acetate → HCID 70416513, compound

HRID 1252264Notes

Reaction equation

HRID 1252264 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5](=[O:33])[C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:10]([C:21](=[O:30])[CH2:22][S:23](=[O:29])(=[O:28])[NH:24][CH:25]([CH3:27])[CH3:26])=[C:9]([CH3:31])[NH:8][C:7]=1[CH3:32].[C:34]([O-:37])(=[O:36])[CH3:35].[Na+]>CN(C)C=O>[C:34]([O:37][CH2:2][CH2:3][O:4][C:5](=[O:33])[C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:10]([C:21](=[O:30])[CH2:22][S:23](=[O:29])(=[O:28])[NH:24][CH:25]([CH3:27])[CH3:26])=[C:9]([CH3:31])[NH:8][C:7]=1[CH3:32])(=[O:36])[CH3:35]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 70416191HCID 70416191, compound

Product 1

HCID 70416513HCID 70416513, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.0 g of 1,4-dihydro-5-[(isopropylsulfamoyl)acetyl]-2,6-dimethyl-4-(3-nitrophenyl)-nicotinic acid 2-chloroethyl ester in 18 ml of dimethylformamide were treated under argon with 0.75 g of dry sodium acetate and the mixture was thereupon heated to reflux for 1 hour. The mixture was then concentrated to dryness under reduced pressure and the residue was partitioned between water and methylene chloride. The organic phase was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and evaporated to dryness. The residual oil was chromatographed on 300 g of silica gel with methylene chloride/ethyl acetate (4:1) as the elution agent. The uniform fractions were combined and evaporated. After triturating the residue with ether there were obtained 1.85 g of 1,4-dihydro-5-[(isopropylsulfamoyl)acetyl]-2,6-dimethyl-4-(3-nitrophenyl)nicotinic acid 2-acetoxyethyl ester in the form of pale yellow crystals, m.p. 133°-136°. Recrystallization from isopropanol yielded a product of melting point 134°-137°.

Workup

  1. temperaturethe mixture was thereupon heated
  2. temperatureto reflux for 1 hour
  3. concentrationThe mixture was then concentrated to dryness under reduced pressure
  4. customthe residue was partitioned between water and methylene chloride
  5. washThe organic phase was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customThe residual oil was chromatographed on 300 g of silica gel with methylene chloride/ethyl acetate (4:1) as the elution agent
  9. customevaporated
  10. customAfter triturating the residue with ether

Sources & evidence

ORD record
ord-2e3d71b29e8644fa90abaacbaf47909d
Source dataset
uspto-grants-1988_05
Patent number
US04742069

Reaction notes

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