Phosphorus oxychloride → HCID 86662180, compound

HRID 1467820Notes

Reaction equation

HRID 1467820 reaction equation
P(Cl)(Cl)(Cl)=[O:2].[CH3:6][N:7]1[C:12]2[C:13]([CH3:16])=[CH:14][NH:15][C:11]=2[C:10](=[O:17])[N:9]([CH3:18])[C:8]1=[O:19]>CN(C)C=O>[CH3:6][N:7]1[C:12]2[C:13]([CH:16]=[O:2])=[CH:14][NH:15][C:11]=2[C:10](=[O:17])[N:9]([CH3:18])[C:8]1=[O:19]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66742610HCID 66742610, compound

Product 1

HCID 86662180HCID 86662180, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

At a temperature of 5-10° C., phosphorous oxychloride (1.84 ml, 20.087 mmol) was mixed with N,N-dimethylformamide (2 mL). Then a solution of Intermediate 1 (600 mg, 3.348 mmol) in N,N-dimethylformamide (3 mL) was added while stirring. The reaction mixture was held for 2 h at 95° C., cooled and poured onto ice (10 g). The precipitate formed was filtered off and recrystallised from water to give 300 mg of the product as an off-white solid; 1H NMR (δ ppm, 300 MHz, DMSO-d6) 3.25 (s, 3H), 3.75 (s, 3H), 8.06 (s, 1H), 9.79 (s, 1H), 13.15 (br s, 1H); APCI-MS (m/z) 208.20 (M+H)+.

Workup

  1. temperaturecooled
  2. additionpoured onto ice (10 g)
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. customrecrystallised from water

Sources & evidence

ORD record
ord-85225bf1c1a1473c883a394df7b87469
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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