Acetone → HCID 6172368, compound

HRID 705465Notes

Reaction equation

HRID 705465 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=O.[CH3:11][C:12]([CH3:14])=[O:13].CC[N:17]([CH2:20][CH3:21])CC.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[C:7]([C:6]1[CH:9]=[CH:10][C:3](/[CH:1]=[CH:11]/[C:12](=[O:13])/[CH:14]=[CH:1]/[C:3]2[CH:10]=[CH:9][C:21]([C:20]#[N:17])=[CH:5][CH:4]=2)=[CH:4][CH:5]=1)#[N:8]

Participants

6

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 660424-Cyanobenzaldehyde

Product 1

HCID 6172368HCID 6172368, compoundYield 125.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-formyl-benzonitrile (1.1 g, 8.4 mmol), acetone (308 μL, 4.2 mmol), LiClO4 (892 mg, 8.4 mmol) and Et3N (117 μL, 0.84 mmol) in toluene (8 mL) was stirred for 2 d at room temperature. A saturated aq. NH4Cl-solution was added to the reaction mixture and the resulting yellow suspension was extracted with CH2Cl2 and the combined organic layers were dried with MgSO4, filtered and evaporated in vacuo to afford NW307.2 as a yellow solid (300 mg, 25%). mp: 137-138° C. 1H NMR (250 MHz, DMSO-d6) δ (ppm): 8.00 (d, 3J=8.3 Hz, 4H, HAr), 7.87 (d, 3J=16.2 Hz, 2H, Hvin), 7.94 (d, 3J=8.4 Hz, 4H, HAr), 7.51 (d, 3J=16.1 Hz, 2H, Hvin). 13C NMR (75 MHz, DMSO-d6) δ (ppm): 188.5 (C), 141.2 (CH), 139.2 (C), 132.8 (CH), 129.2 (CH), 128.4 (CH), 118.6 (C), 112.4 (C). MS (FAB) m/z: 285.19 (M+). Anal. calcd for C19H12N2O: C, 80.27; H, 4.25; N, 9.85. Found: C, 80.04; H, 4.28; N, 9.76%.

Workup

  1. extractionthe resulting yellow suspension was extracted with CH2Cl2
  2. dry with materialthe combined organic layers were dried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-789dcef173534802b2750736439a0d4d
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

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