Hydrochloric Acid → HCID 21094303, compound

HRID 1350090Notes

Reaction equation

HRID 1350090 reaction equation
[CH2:1]=O.[ClH:3].[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][NH:11][CH2:10][CH:9]2[CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20].Cl>C(O)=O>[ClH:3].[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][N:11]([CH3:1])[CH2:10][CH:9]2[CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 21094293HCID 21094293, compound

Product 1

HCID 21094303HCID 21094303, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Formic acid (0.55 ml) and 37% formaldehyde (0.6 ml) are added at 0° C. to the compound obtained in Example 4 (1.8 g; 7.2 mmol) in the form of a base. The reaction mixture is heated at 80° C. for 24 hours with stirring. After having cooled the reaction mixture to 0° C., 10 ml of 6N HCl are added. The mixture is then washed with ether, rendered alkaline with 2N NaOH and extracted with ether. The organic phase is dried over magnesium sulphate, filtered and evaporated under reduced pressure. The yellow oil so obtained is purified by chromatography on silica gel (eluant: dichloromethane with the progressive addition of methanol until the proportions 9/1 are reached). The purified oil is taken up in ether saturated with HCl(g) and stirred until a precipitate is obtained, which precipitate is then suction-filtered off and placed under a vacuum in a dessicator to yield the title product in the form of a very hygroscopic white solid.

Workup

  1. temperatureAfter having cooled the reaction mixture to 0° C.
  2. washThe mixture is then washed with ether
  3. extractionextracted with ether
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe yellow oil so obtained
  8. customis purified by chromatography on silica gel (eluant
  9. additiondichloromethane with the progressive addition of methanol until the proportions 9/1
  10. stirringstirred until a precipitate
  11. customis obtained
  12. filtrationwhich precipitate is then suction-filtered off

Sources & evidence

ORD record
ord-c340add2af6e4eba9f4e9e02032b7df3
Source dataset
uspto-grants-2007_05
Patent number
US07214689B2

Reaction notes

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