Dimethylformamide → HCID 12056850, compound

HRID 1835861Notes

Reaction equation

HRID 1835861 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([N:9]([CH2:14][CH3:15])[C:10](=[O:13])[CH2:11]Cl)[CH3:8].CN(C=O)C.[Cl:21][C:22]1[C:31]([OH:32])=[C:30]([S:33]([CH2:36][CH3:37])(=[O:35])=[O:34])[CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25]>O>[Cl:21][C:22]1[C:31]([O:32][CH2:11][C:10]([N:9]([CH2:14][CH3:15])[CH2:7][CH3:8])=[O:13])=[C:30]([S:33]([CH2:36][CH3:37])(=[O:35])=[O:34])[CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 16844Chloro-N,N-diethylacetamideHCID 15906661HCID 15906661, compound

Product 1

HCID 12056850HCID 12056850, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

0.922 g (7.2 mmol) of K2CO3, 0.179 g (1.10 mmol) of Kl and 0.644 g (4.3 mmol) of N,N-diethylchloroacetamide were introduced into 30 ml of DMF. 1.000 g (3.6 mmol) of methyl 2-chloro-3-hydroxy-4-ethylsulfonylbenzoate were added at RT and the mixture was then heated for 7 hours at 120° C. The mixture was then poured into water and extracted with diisopropyl ether. The organic phases were washed with water, dried over Na2SO4 and concentrated completely. Chromatography on silica gel (eluent: n-heptane/ethyl acetate 1:1) gave methyl 2-chloro-3-(N,N-diethylaminocarbonylmethoxy) -4-ethylsulfonylbenzoate as a colorless viscous oil.

Workup

  1. extractionextracted with diisopropyl ether
  2. washThe organic phases were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated completely

Sources & evidence

ORD record
ord-a533e0c522bd44e6a7392830f1e1afba
Source dataset
uspto-grants-2004_08
Patent number
US06774086B2

Reaction notes

Loading…