Dimethylamine → HCID 83383404, compound

HRID 1968040Notes

Reaction equation

HRID 1968040 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)(Cl)=O.[CH3:17][NH:18][CH3:19]>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][C:3]=1[C:4]([N:18]([CH3:19])[CH3:17])=[O:5]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 24386Thionyl ChlorideHCID 185259462-Fluoro-5-formylbenzoic acid

Product 1

HCID 83383404HCID 83383404, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The solution of 2-fluoro-5-formylbenzoic acid (3 g, 17.8 mmol) in methylene chloride (10 mL) was added thionyl chloride (2.0 mL, 26.7 mmol) slowly at 0° C. Then the cold reaction mixture was heated to reflux for 3 h. The solution was cooled to 0° C., added dimethylamine (40 wt. % solution in water, 5 mL) slowly, and then stirred at room temperature for 1 h. The solution was washed with water and brine, the organic layer was dried with Na2SO4 and the solvent was removed to get the desired product (2.4 g, yield 76%). LC-MS (ESI) m/z: 196 (M+1)+

Workup

  1. customThen the cold reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 3 h
  4. washThe solution was washed with water and brine
  5. dry with materialthe organic layer was dried with Na2SO4
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-c955b2d004924f0b8e01d52a1f695181
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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