Methane → HCID 86757983, compound

HRID 843656Notes

Reaction equation

HRID 843656 reaction equation
O.[CH2:2]([N:5]([CH:9]=[C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH2:11]1)[CH2:6][CH2:7][CH3:8])[CH2:3][CH3:4].C>Cl>[CH2:2]([N:5]([CH:9]=[C:10]1[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:18][CH2:19]1)[CH2:6][CH2:7][CH3:8])[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 297MethaneHCID 962WaterHCID 86757982HCID 86757982, compound

Product 1

HCID 86757983HCID 86757983, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

9 cm3 of distilled water are added to an oily suspension of 2.4 g of methyl 4-(N,N-di-n-propylaminomethylene)benzoate in 9 cm3 of concentrated hydrochloric acid (36% minimum), at a temperature close to 20° C. The reaction mixture is heated under reflux for 24 hours and then supplemented with 3S charcoal, and filtered while hot on a sintered glass. The filtrate is concentrated to dryness under reduced pressure (about 1 kPa) at a temperature close to 40° C. The white solid thus obtained is filtered on sintered glass, rinsed with 3 times 10 cm3 of acetonitrile, 10 cm3 of diisopropyl ether, air-dried and then dried under reduced pressure (about 0.2 kPa) at a temperature close to 50° C. 1.8 g of 4-(N,N-di-n-propylaminomethylene)benzoic acid (monohydrochloride) are thus obtained in the form of white crystals.

Workup

  1. customclose to 20° C
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 24 hours
  4. filtrationfiltered while hot on a sintered glass
  5. concentrationThe filtrate is concentrated to dryness under reduced pressure (about 1 kPa) at a temperature
  6. customclose to 40° C
  7. customThe white solid thus obtained
  8. filtrationis filtered on sintered glass
  9. washrinsed with 3 times 10 cm3 of acetonitrile, 10 cm3 of diisopropyl ether
  10. customair-dried
  11. customdried under reduced pressure (about 0.2 kPa) at a temperature
  12. customclose to 50° C

Sources & evidence

ORD record
ord-0eddcec61eee4293985d19906bbc0eba
Source dataset
uspto-grants-2002_04
Patent number
US06380197B1

Reaction notes

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