Dimethylformamide → HCID 22340631, compound

HRID 585322Notes

Reaction equation

HRID 585322 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl[CH2:8][C:9](=[O:11])[CH3:10].CN(C=O)C.[Cl:17][C:18]1[C:27]([OH:28])=[C:26]([S:29]([CH2:32][CH3:33])(=[O:31])=[O:30])[CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21]>O>[Cl:17][C:18]1[C:27]([O:28][CH2:8][C:9]([CH3:10])=[O:11])=[C:26]([S:29]([CH2:32][CH3:33])(=[O:31])=[O:30])[CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 15906661HCID 15906661, compound

Product 1

HCID 22340631HCID 22340631, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

0.922 g (7.2 mmol) of K2CO3, 0.179 g (1.10 mmol) of KI and 0.454 g (4.7 mmol) of chloroacetone 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 4 hours at 80° C. The mixture was then poured into water and extracted with diisopropyl ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated to dryness. The resulting crude methyl 2-chloro-3-(methylcarbonylmethoxy)-4-ethylsulfonyl benzoate viscous oil was sufficiently pure for the subsequent reactions.

Workup

  1. extractionextracted with diisopropyl ether
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-0d2cc3ba0ab04e398268d5b1703bda42
Source dataset
uspto-grants-2005_08
Patent number
US06930208B2

Reaction notes

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