Phosphorus oxychloride → HCID 59594371, compound

HRID 1930232Notes

Reaction equation

HRID 1930232 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:7](=[O:12])[CH2:8][NH:9][C:10](=O)[C:4]=2[CH:3]=1.O=P(Cl)(Cl)[Cl:26]>C1(C)C=CC=CC=1>[Cl:26][C:10]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:23]=[CH:22][C:5]=2[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:7](=[O:12])[CH2:8][N:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59594400HCID 59594400, compound

Product 1

HCID 59594371HCID 59594371, compoundYield 120%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 1 L 3-neck RBF equipped with magnetic stir bar, condenser and N2 inlet, C2 (45 g, 0.136 mol) was suspended in 400 mL of toluene. To this was added N,N-dimethylanaline (33 g, 0.272 mol) followed by the addition of POCl3 (23 g) and the reaction stirred for 3 min (RT). Reaction flask was placed into a 90° C. oil bath and the reaction mixture was heated for 5 h and then cooled. The reaction was quenched by adding 450 mL of ice water and stirred for 15 min. Organic layer was separated and quickly washed with cold water (2×250 mL) and brine (300 mL). Organic layer was dried over MgSO4, filtered and concentrated on a rotary evaporator to give 57 g of black crude product. Crude product was used for next step with no further purification. Yield 87.5%.

Workup

  1. customIn a 1 L 3-neck RBF equipped with magnetic stir bar, condenser and N2 inlet
  2. additionTo this was added N,N-dimethylanaline (33 g, 0.272 mol)
  3. customReaction flask
  4. customwas placed into a 90° C.
  5. temperaturethe reaction mixture was heated for 5 h
  6. temperaturecooled
  7. customThe reaction was quenched
  8. additionby adding 450 mL of ice water
  9. stirringstirred for 15 min
  10. customOrganic layer was separated
  11. washquickly washed with cold water (2×250 mL) and brine (300 mL)
  12. dry with materialOrganic layer was dried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-38acbe31c1fa403fbb490be751a572c7
Source dataset
uspto-grants-2012_05
Patent number
US08188072B2

Reaction notes

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