Hydrochloric Acid → HCID 178439384, compound

HRID 2206448Notes

Reaction equation

HRID 2206448 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([N:14]([CH3:16])[CH3:15])[CH:7]=[C:8]([CH:11]([CH3:13])[CH3:12])[C:9]=1[NH2:10])([CH3:3])[CH3:2].C=O.Cl.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]=O.[C:28]1([B-:34]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Na+]>C(O)C.CO>[C:47]1([B-:34]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1.[CH3:15][N:14]([CH3:16])[C:6]1[CH:5]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:9]([N:10]2[CH:26]=[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][N+:20]3=[CH:28]2)=[C:8]([CH:11]([CH3:12])[CH3:13])[CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 142732-PyridinecarboxaldehydeHCID 2723787Sodium TetraphenylborateHCID 53740991HCID 53740991, compound

Product 1

HCID 178439384HCID 178439384, compoundYield 142.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

was prepared according to general procedure (A); 77 μg 3,5-diisopropyl-N,N-dimethylbenzene-1,4-diamine (0.35 mmol, 1 equiv), 39 μl formalin (0.53 mmol, 1.5 equiv), 0.23 mL 3.05 M hydrochloric acid in ethanol (0.70 mmol, 2 equiv) and 34 μl picolinaldehyde (0.35 mmol, 1 equiv) were combined in 1.8 mL ethanol and maintained at room temperature for 12 hours. The reaction was concentrated in vacuo and dried under high vacuum at 0.2 Torr. The crude material was then dissolved in 2.5 mL ethanol and stirred with 0.8 g sodium bicarbonate for 30 minutes at room temperature. The resulting suspension was then filtered through a 0.2 um nylon syringe tip filter. The solid sodium bicarbonate was washed with ethanol three times using 0.5 mL of ethanol for each wash and filtered. The combined filtrate was concentrated. The resulting crude oil was dissolved in 3.0 mL methanol and 0.12 g sodium tetraphenylborate (0.35 mmol, 1 equiv) in 1.0 mL methanol was added drop wise while stirring vigorously. The mixture was cooled to 4° C. in a refrigerator. The methanol was then decanted, and the solid was rinsed with methanol three times using 0.25 mL of methanol for each rinse and dried under high vacuum at 0.2 Torr to obtain 0.16 g 2-(4-(dimethylamino)-2,6-diisopropylphenyl)-2H-imidazo[1,5-a]pyridin-4-ium tetraphenylborate (0.26 mmol, a 73% yield) as a dark brown solid.

Workup

  1. customwas prepared
  2. concentrationThe reaction was concentrated in vacuo
  3. customdried under high vacuum at 0.2 Torr
  4. dissolutionThe crude material was then dissolved in 2.5 mL ethanol
  5. filtrationThe resulting suspension was then filtered through a 0.2 um nylon syringe tip
  6. filtrationfilter
  7. washThe solid sodium bicarbonate was washed with ethanol three times
  8. washeach wash
  9. filtrationfiltered
  10. concentrationThe combined filtrate was concentrated
  11. dissolutionThe resulting crude oil was dissolved in 3.0 mL methanol
  12. stirringwhile stirring vigorously
  13. temperatureThe mixture was cooled to 4° C. in a refrigerator
  14. customThe methanol was then decanted
  15. washthe solid was rinsed with methanol three times
  16. washeach rinse
  17. customdried under high vacuum at 0.2 Torr

Sources & evidence

ORD record
ord-0e9f554ff6b14554833cfd05ba566b7c
Source dataset
uspto-grants-2016_06
Patent number
US09371448B2

Reaction notes

Loading…