Dimethylformamide → HCID 178441973, compound

HRID 1162767Notes

Reaction equation

P(Cl)(Cl)(Cl)=O.CN([CH:9]=[O:10])C.[CH3:11][C:12](=[N:17][NH:18][C:19](N)=O)[C:13]([CH3:16])([CH3:15])[CH3:14].[OH-].[Na+]>O.C(OCC)C>[C:13]([C:12]1[C:11]([CH:9]=[O:10])=[CH:19][NH:18][N:17]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 60 °C

Procedure

Phosphorus oxychloride (18.2 mL, 195 mmol) was added portionwise to DMF (30 mL, 387 mmol) at <5° C. Pinacolone semicarbazone (15.4 g, 97.6 mmol) was added over 1 h maintaining the temperature at <5° C. The reaction mixture became very thick so an additional quantity of DMF (10 mL) was added. The mixture was heated to 60° C. for 3.5 h then allowed to cool and poured into ice. The reaction was neutralised using sodium hydroxide (40 g, 1 mol) in water (130 mL) then heated at 60° C. for 5 min. The mixture was cooled in an ice bath and acidified to pH 6 and the product extracted into EtOAc. The EtOAc was dried over MgSO4 and concentrated onto silica. The crude product was purified by flash chromatography using eluants EtOAc/heptane. Trituration in diethyl ether gave a white solid (1.02 g, 6.1 mmol, 6%).

Workup

temperaturemaintaining the temperature at <5° C
additionwas added
temperatureto cool
additionpoured into ice
temperaturethen heated at 60° C. for 5 min
temperatureThe mixture was cooled in an ice bath
extractionthe product extracted into EtOAc
dry with materialThe EtOAc was dried over MgSO4
concentrationconcentrated onto silica
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-0ca7b27946e04c8b8be903e7c7f6a48e
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820707B2

Reaction notes

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