Bromazepam → HCID 178482308, compound

HRID 1075748Notes

Reaction equation

HRID 1075748 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=O)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1.O1CCCC1.[CH3:25][NH2:26]>[Ti](Cl)(Cl)(Cl)Cl.C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:26][CH3:25])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1

Participants

6

Reactant 3

HCID 2441BromazepamHCID 6329MethylamineHCID 8028Tetrahydrofuran

Product 1

HCID 178482308HCID 178482308, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent2×

Procedure

A solution of 63.2 g. (0.2 mol) of 7-bromo-1,3-dihydro-5-(2-pyridyl)-2H-1,4-benzodiazepin-2-one in 1.7 l. of tetrahydrofuran and 400 ml. of benzene was saturated with methylamine. A solution of 45.5 g. of titanium tetrachloride in 400 ml. of benzene was added slowly with ice cooling. After addition was complete, the reaction mixture was stirred and refluxed for 2 hours. It was then partitioned between water and methylene chloride. The organic layer was dried over sodium sulfate and evaporated. Crystallization from methylene chloride/hexane yielded 7-bromo-2-methylamino-5-(2-pyridyl)-3H-1,4-benzodiazepine, having a melting point of 208°-214°.

Workup

  1. additionAfter addition
  2. temperaturerefluxed for 2 hours
  3. customIt was then partitioned between water and methylene chloride
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated
  6. customCrystallization from methylene chloride/hexane

Sources & evidence

ORD record
ord-e481c223ee914674abd20bb8e460d1be
Source dataset
uspto-grants-1976_05
Patent number
US03954728

Reaction notes

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