Hydrochloric Acid → HCID 178448596, compound

HRID 2206443Notes

Reaction equation

HRID 2206443 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].C=O.Cl.[CH2:9](O)C.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=O.[C:27]1([B-:33]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Na+]>C(#N)C.CO>[C:46]1([B-:33]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1.[CH2:1]([N:5]1[C:18]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)=[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N+:12]2=[CH:9]1)[CH2:2][CH2:3][CH3:4]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 702EthanolHCID 712FormaldehydeHCID 8007ButylamineHCID 2723787Sodium TetraphenylborateHCID 3018781(4-Methylphenyl)(pyridin-2-yl)methanone

Product 1

HCID 178448596HCID 178448596, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6342AcetonitrileSolvent

Procedure

was prepared according to general procedure (A), in which 25 μl n-butylamine (0.25 mmol, 1 equiv), 28 μl formalin (0.37 mmol, 1.5 equiv), 82 μl 3.05 M hydrochloric acid in ethanol (0.25 mmol, 1 equiv) and 49 mg pyridin-2-yl(p-tolyl)methanone (0.25 mmol, 1 equiv) were combined in 0.50 mL acetonitrile and maintained at room temperature for 12 hours. The crude material was then dissolved in 1.0 mL methanol and then 94 mg sodium tetraphenylborate (0.27 mmol, 1.1 equiv) in 1.0 mL methanol was added drop wise while stirring vigorously. The heterogeneous mixture was stirred vigorously for 3 hours at room temperature until the solid became a fine suspension, which was then filtered, washed with 500 μl of methanol and dried under high vacuum at 0.2 Torr to obtain 105 mg 2-butyl-1-(p-tolyl)-2H-imidazo[1,5-a]pyridin-4-ium tetraphenylborate (0.18 mmol, a 72% yield) as a white solid.

Workup

  1. customwas prepared
  2. stirringThe heterogeneous mixture was stirred vigorously for 3 hours at room temperature until the solid
  3. filtrationwas then filtered
  4. washwashed with 500 μl of methanol
  5. customdried under high vacuum at 0.2 Torr

Sources & evidence

ORD record
ord-be05a3522839429a8713492dac078490
Source dataset
uspto-grants-2016_06
Patent number
US09371448B2

Reaction notes

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