Dimethylformamide → HCID 86677513, compound

HRID 2174535Notes

Reaction equation

HRID 2174535 reaction equation
O=P(Cl)(Cl)Cl.[CH3:6][N:7]([CH3:25])[C:8]1[CH:13]=[N:12][N:11]([CH:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16]([CH3:23])([CH3:22])[CH2:15]2)[C:10](=[O:24])[CH:9]=1.CN([CH:29]=[O:30])C>>[CH3:25][N:7]([CH3:6])[C:8]1[CH:13]=[N:12][N:11]([CH:14]2[CH2:19][C:18]([CH3:20])([CH3:21])[CH2:17][C:16]([CH3:23])([CH3:22])[CH2:15]2)[C:10](=[O:24])[C:9]=1[CH:29]=[O:30]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 53353778HCID 53353778, compound

Product 1

HCID 86677513HCID 86677513, compoundYield 100%

Procedure

POCl3 (0.9 mL, 9.75 mmol) was slowly added to precooled (0° C.), anhydrous DMF (5 mL). After stirring at room temperature for 30 min, a solution of 5-dimethylamino-2-(3,3,5,5-tetramethyl-cyclohexyl)-2H-pyridazin-3-one (749 mg, 2.70 mmol) in anhydrous DMF (6 mL) was added and the mixture was stirred at 70° C. for 1.5 h. After cooling, the mixture was poured over saturated NaHCO3/ice. The aqueous layer was extracted with EtOAc (2×20 mL). The combined organics were dried (Na2SO4), filtered and evaporated in vacuo to provide 5-dimethylamino-3-oxo-2-(3,3,5,5-tetramethyl-cyclohexyl)-2,3-dihydro-pyridazine-4-carbaldehyde (1.19 g, 100%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 10.33 (1H, s), 7.80 (1H, s), 5.27 (1H, app tt, J=3.7, 11.7 Hz), 3.13 (6H, s), 1.63-1.44 (4H, m), 1.30 (2H, app t, J=11.0 Hz), 1.16 (6H, s), 0.98 (6H, s).

Workup

  1. stirringthe mixture was stirred at 70° C. for 1.5 h
  2. temperatureAfter cooling
  3. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-139841e194af47d7a1e4b87044f380d1
Source dataset
uspto-grants-2015_06
Patent number
US09062004B2

Reaction notes

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