Phosphorus oxychloride → HCID 68156097, compound

HRID 1877797Notes

Reaction equation

HRID 1877797 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:16][C:15](=O)[C:14]3=[CH:18][C:19]([CH3:21])=[CH:20][N:13]3[CH2:12][C:11]=2[CH:22]=1>C(Cl)Cl>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:16]=[C:15]([Cl:3])[C:14]3=[CH:18][C:19]([CH3:21])=[CH:20][N:13]3[CH2:12][C:11]=2[CH:22]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 68155891HCID 68155891, compound

Product 1

HCID 68156097HCID 68156097, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add phosphoryl chloride (1.47 mL, 2.43 g, 15.85 mmoles) to 7-chloro-2-methyl-5,10-dihydro-11H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one (1.117 g, 4.53 mmoles) in DCM (50 mL) and stir at room temperature over a weekend. Add ice water to the reaction mixture then add DCM, separate the aqueous layer and wash the DCM layer with water and sodium hydrogen carbonate solution. Dry the DCM solution with MgSO4, filter and evaporate the solvent in vacuo to give 7,11-dichloro-2-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine (1.167 g).

Workup

  1. customAdd ice water to the reaction mixture then add DCM, separate the aqueous layer
  2. washwash the DCM layer with water and sodium hydrogen carbonate solution
  3. dry with materialDry the DCM solution with MgSO4
  4. filtrationfilter
  5. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-686594d8c3244bc798bc3a24339860a8
Source dataset
uspto-grants-2012_11
Patent number
US08314092B2

Reaction notes

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