Water → HCID 13649489, compound

HRID 1982384Notes

Reaction equation

HRID 1982384 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][C:6](=O)[C:5]=12.P(Cl)(Cl)([Cl:18])=O.O.[OH-].[NH4+]>C(Cl)Cl>[Cl:18][C:6]1[C:5]2=[CH:1][CH:2]=[CH:3][N:4]2[CH2:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 4682545,10-Dihydro-11H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one

Product 1

HCID 13649489HCID 13649489, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of 881 g of 10,11-dihydro-5-H-pyrrolo-[2,1-c][1,4]benzodiazepin-11-one is stirred in 12 L of methylene chloride, and 819 g of 99% phosphorus oxychloride is added all at once. The mixture is stirred and refluxed for 19 hours. The reaction mixture is cooled to room temperature. A mixture of 5 L of crushed ice, 7.5 L of cold water and 1.81 kg of 28% ammonium hydroxide solution is stirred and 1.25 L portions of the reaction mixture are added over a period of 15 minutes. The reaction temperature is kept below 25° during the addition. After stirring for 15 minutes, the layers are separated, the methylene chloride layer is washed by stirring with 1 L of cold water then dried by stirring with magnesium sulfate for 1 hour. Charcoal (90 g) is added and the mixture is filtered through filter-cel. The methylene chloride solution is concentrated to dryness in vacuo to give 11-chloro-5H-pyrrolo[2,1-c][1,4]benzodiazepine, m.p. 102°-104°.

Workup

  1. temperaturerefluxed for 19 hours
  2. stirringis stirred
  3. addition1.25 L portions of the reaction mixture are added over a period of 15 minutes
  4. additionThe reaction temperature is kept below 25° during the addition
  5. stirringAfter stirring for 15 minutes
  6. customthe layers are separated
  7. washthe methylene chloride layer is washed
  8. stirringby stirring with 1 L of cold water
  9. customthen dried
  10. stirringby stirring with magnesium sulfate for 1 hour
  11. additionCharcoal (90 g) is added
  12. filtrationthe mixture is filtered
  13. filtrationthrough filter-cel
  14. concentrationThe methylene chloride solution is concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-4ab07e2d263149729e516147b6fd40f4
Source dataset
uspto-grants-1986_06
Patent number
US04596799

Reaction notes

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