Carbon Dioxide → 2,3-Dihydro-2-(2-hydroxyethyl)-3-oxo-5,6-diphenyl-4-pyridazinecarbonitrile

HRID 463967Notes

Reaction equation

[C:1]([C:3]1[C:4](=[O:21])[NH:5][N:6]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)#[N:2].[OH-].[K+].C1(=O)O[CH2:27][CH2:26][O:25]1.C(=O)=O>CN(C)C=O>[OH:25][CH2:26][CH2:27][N:5]1[C:4](=[O:21])[C:3]([C:1]#[N:2])=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:6]1

Participants

Conditions

Temperature: 100 °C

Procedure

17.7 grams (0.065 mole) of the product of Example 1 was dissolved in 60 mls of dry dimethylformamide along with 0.25 grams of potassium hydroxide and 7.5 grams (0.085 mole) of ethylene carbonate. The mixture was heated to 100° C. and maintained for 2 hours until no carbon dioxide was liberated. The solution was then heated at 110° C. for 30 minutes. The solution was filtered and the dimethylformamide was distilled under reduced pressure with a mechanical pump. The solid was dried in a drying pistol using xylene as the solvent. The residual solid was recrystallized from ethyl alcohol to give 10.4 grams (50%) yield of a solid melting at 197°-198° C. Calculated for C19H15N3O2, C, 71.9; H, 4.8; N, 13.2. Found: C, 71.7; H, 4.71; N, 13.5. The infrared spectra showed the OH group at 2.9μ, the nitrile band at 4.5μ, and the carbonyl band at 6.0μ. The NMR confirmed that the product was the desired material.

Workup

temperatureThe solution was then heated at 110° C. for 30 minutes
filtrationThe solution was filtered
distillationthe dimethylformamide was distilled under reduced pressure with a mechanical pump
customThe solid was dried in a drying pistol
customThe residual solid was recrystallized from ethyl alcohol

Sources & evidence

ORD record: ord-3468c7ff5ceb4edf87491389effe7d2b
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04545810

Reaction notes

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