Ammonia → Medazepam

HRID 441939

Reaction equation

HRID 441939 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>[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:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 3016DiazepamHCID 6328200Diboron

Product 1

HCID 4041MedazepamYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 30 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 -15° to -10° C. After further stirring at -10° C for 2 hours, the reaction mixture was poured into 100 ml of ice-water and 20 ml of concentrated hydrochloric acid was added thereto. The mixture was reflexed for one hour. After having been cooled, the resultant red solution was neutralized with 28%-aqueous ammonia, and then extracted with ether. The ether extract was washed with water and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. There were obtained 1.35 g of 1-methyl-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepine, which were recrystallized from n-hexane to give prisms melting at 99.5° to 101,0° C.

Workup

  1. additionwas added
  2. waitThe mixture was reflexed for one hour
  3. temperatureAfter having been cooled
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-77475ec902224a74a78976d778490fb4
Source dataset
uspto-grants-1977_08
Patent number
US04044003

Linked notes

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