Dimethylamine → HCID 67696209, compound

HRID 611143Notes

Reaction equation

HRID 611143 reaction equation
[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([N:18]3[CH2:23][CH2:22][C:21]4[CH:24]=[CH:25][O:26][C:20]=4[CH2:19]3)=[O:17])=[CH:11][C:10]=2[S:9](=[O:28])(=[O:27])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[CH3:29][NH:30][CH3:31].[CH2:32]=O>C(O)(=O)C>[CH3:29][N:30]([CH2:32][C:25]1[O:26][C:20]2[CH2:19][N:18]([C:16]([C:12]3[CH:13]=[CH:14][C:15]4[C:2](=[O:1])[C:3]5[C:8]([S:9](=[O:28])(=[O:27])[C:10]=4[CH:11]=3)=[CH:7][CH:6]=[CH:5][CH:4]=5)=[O:17])[CH2:23][CH2:22][C:21]=2[CH:24]=1)[CH3:31]

Participants

5

Reactant 3

HCID 674Dimethylamine2×HCID 712Formaldehyde2×HCID 67696284HCID 67696284, compound

Product 1

HCID 67696209HCID 67696209, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.240 g (0.610 mmol) of 6-(9,10,10-trioxo-9,10-dihydro-10λ6 -thioxanthene-3-carbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 20 ml of acetic acid, 0.083 ml (0.92 mmol) of 50% aqueous dimethylamine and 0.075 ml (0.92 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 60 minutes. Additionally, 0.083 ml (0.92 mmol) of 50% aqueous dimethylamine and 0.075 ml (0.92 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 60 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate, and extracted with dichloromethane 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform to chloroform/methanol=25/1) to yield the desired product.

Workup

  1. stirringby stirring at 100° C. for 60 minutes
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. extractionextracted with dichloromethane 2 times
  4. washThe combined organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting crude product was purified by silica gel column chromatography (chloroform to chloroform/methanol=25/1)

Sources & evidence

ORD record
ord-c79708208db448dba9d2633148270974
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

Loading…