Phosphorus oxychloride → HCID 59594371, compound

HRID 2263683Notes

Reaction equation

HRID 2263683 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, 7-chloro-1-(4-methoxybenzyl)-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione (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. The organic layer was separated and quickly washed with cold water (2×250 mL) and brine (300 mL). Then, the 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. additionTo this was added N,N-dimethylanaline (33 g, 0.272 mol)
  2. customReaction flask
  3. customwas placed into a 90° C.
  4. temperaturethe reaction mixture was heated for 5 h
  5. temperaturecooled
  6. customThe reaction was quenched
  7. additionby adding 450 mL of ice water
  8. stirringstirred for 15 min
  9. customThe organic layer was separated
  10. washquickly washed with cold water (2×250 mL) and brine (300 mL)
  11. dry with materialThen, the organic layer was dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-70573963eb4a4f13a22434a0a2bc3da7
Source dataset
uspto-grants-2010_12
Patent number
US07851465B2

Reaction notes

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