Ammonia → HCID 12234597, compound

HRID 441942Notes

Reaction equation

HRID 441942 reaction equation
B#B.[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=2[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:7][CH2:6][C:5]1=O.Cl.N>O1CCCC1.O>[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=2[CH:8]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:7][CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 3016DiazepamHCID 6328200Diboron2×

Product 1

HCID 12234597HCID 12234597, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 50 ml of 1.07 M diborane in tetrahydrofuran was added with stirring 1.43 g of 1-methyl-5-phenyl-7-chloro-1,3-dihydro-2H-1,4-benzodiazepin-2-one at room temperature, and the mixture was refluxed with stirring for 7.5 hours. After having been left standing overnight, 5 ml of water followed by 5 ml concentrated hydrochloric acid was added to decompose the excess diborane, and the mixture was refluxed for one hour. After cooling, the solution was neutralized with concentrated ammonia, and extracted with ether. The ether extract was washed with water and dried over anhydrous sodium sulfate, and the solvent was ramoved under reduced pressure. The residue was recrystallized from n-pentane to obtain 1.30 g of 1-methyl-5-phenyl-7-chloro-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, melting at 66° to 68° C.

Workup

  1. temperaturethe mixture was refluxed
  2. waitAfter having been left
  3. waitstanding overnight
  4. additionwas added
  5. temperaturethe mixture was refluxed for one hour
  6. temperatureAfter cooling
  7. extractionextracted with ether
  8. extractionThe ether extract
  9. washwas washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe residue was recrystallized from n-pentane

Sources & evidence

ORD record
ord-51a84dbc7aae4eac81fc240a60e46db8
Source dataset
uspto-grants-1977_08
Patent number
US04044003

Reaction notes

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