Dimethyl Sulfoxide → HCID 59177867, compound

HRID 1875435Notes

Reaction equation

HRID 1875435 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[O:22])[CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])C(OC)=O)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl-].[Na+].CS(C)=O>O>[Cl:1][C:2]1[C:3]([C:9](=[O:22])[CH2:10][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 59177868Methyl 3-(3,5-dichloropyridin-2-yl)-2-(2-fluorophenyl)-3-oxopropanoate

Product 1

HCID 59177867HCID 59177867, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
150 °C

Procedure

A mixture of 4.50 g (13.2 mmol) of methyl 3-(3,5-dichloropyridin-2-yl)-2-(2-fluorophenyl)-3-oxopropanoate from example 1A, 845 mg (14.5 mmol) of sodium chloride, 474 mg (26.3 mmol) of water and 13.5 ml of DMSO is heated in a microwave at 150° C. for 10 min and then stirred into water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated. The residue is purified by chromatography on silica gel (eluent: dichloromethane) to result in a yellow oil which gradually crystallizes and affords 3.18 g (85% of theory) of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue is purified by chromatography on silica gel (eluent: dichloromethane)
  5. customto result in a yellow oil which
  6. customgradually crystallizes

Sources & evidence

ORD record
ord-191caca329264534bddcfb489060d957
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

Loading…