Phosphorus oxychloride → HCID 178440023, compound

HRID 1957945Notes

Reaction equation

HRID 1957945 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH3:20])[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][C:5]=1[C:21]1[NH:26][C:25](=[O:27])[C:24]([CH:28]([NH:30][C:31](=O)[CH2:32][CH2:33][CH3:34])[CH3:29])=[N:23][N:22]=1)[CH3:2].O=P(Cl)(Cl)Cl>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH3:20])[CH2:15][CH2:14]2)(=[O:11])=[O:12])=[CH:6][C:5]=1[C:21]1[NH:22][N:23]2[C:31]([CH2:32][CH2:33][CH3:34])=[N:30][C:28]([CH3:29])=[C:24]2[C:25](=[O:27])[N:26]=1)[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135884971HCID 135884971, compound

Product 1

HCID 178440023HCID 178440023, compoundYield 65.5%

Conditions

Temperature
80 °C

Procedure

The compound of formula III (0.51 g, 1 mmol) was added with POCl3 (2 mL), and the mixture was heated for 2 hours at 80° C. The excess phosphorous oxychloride was evaporated of under reduced pressure, and the residue was slowly poured into chopped ice. The solution was adjusted to a pH of 8 with sodium carbonate, and extracted with dichloromethane (40 mL). The organic phase was washed with saturated saline (15 mL), and dried over anhydrous sodium sulfate. Then, 20 mL of ethanol was added therein, and the solution was decolorized by activated carbon, filtrated, and evaporated to remove some of the solvent therefrom. Ethyl acetate was then added therein to perform a recrystallization. Finally, the crystal was separated to obtain 0.32 g of product with a yield of 65%. 1H NMR (CDCl3, 300 MHz) δ: 1.01 (3H, t), 1.04 (3H, t), 1.62 (3H, t), 1.86 (2H, m), 2.42 (2H, q), 2.54 (4H, t), 2.64 (3H, s), 2.99 (2H, t), 3.07 (4H, m), 4.34 (2H, q), 7.15 (1H, d), 7.88 (1H, dd), 8.48 (1H, d), 9.52 (1H, s).

Workup

  1. customThe excess phosphorous oxychloride was evaporated of under reduced pressure
  2. additionthe residue was slowly poured into chopped ice
  3. extractionextracted with dichloromethane (40 mL)
  4. washThe organic phase was washed with saturated saline (15 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. additionThen, 20 mL of ethanol was added
  7. filtrationfiltrated
  8. customevaporated
  9. customto remove some of the solvent
  10. additionEthyl acetate was then added
  11. customa recrystallization
  12. customFinally, the crystal was separated

Sources & evidence

ORD record
ord-77714ba72a3d4b11a3e02ed0e29c7fe3
Source dataset
uspto-grants-2013_04
Patent number
US08410098B2

Reaction notes

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