Acetic Acid → 8-chloro-4-(nitrosomethylamino)-1-phenyl-3H-1,5-benzodiazepin-2-one

HRID 1763239Notes

Reaction equation

HRID 1763239 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([NH:18][CH3:19])[CH2:8][C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C(O)(=O)C.[N:26]([O-])=[O:27].[Na+]>O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([NH:18][CH2:19][N:26]=[O:27])[CH2:8][C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23668193Sodium NitriteHCID 178482322HCID 178482322, compound

Product 1

HCID 1785263748-chloro-4-(nitrosomethylamino)-1-phenyl-3H-1,5-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6 g (0.02 mol) of 7-chloro-3,5-dihydro-2-methylamino-5-phenyl-4H-1,5-benzodiazepin-4-one, 25 ml of glacial acetic acid and 1.75 g (0.025 mol) of sodium nitrite was stirred stirred at 10°-20° for 1 hr. The reaction mixture was diluted with ice and water and stirred for another 15 min. The precipitated material was collected and dissolved in methylene chloride. The solution was washed with sodium bicarbonate solution, dried over sodium sulfate and evaporated. Crystallization from methylene chloride/hexane yielded the above-named product as yellow crystals, with mp 120°-125°. For analysis it was recrystallized like form methylene chloride/hexane, mp. 122°-125°.

Workup

  1. stirringstirred at 10°-20° for 1 hr
  2. stirringstirred for another 15 min
  3. customThe precipitated material was collected
  4. dissolutiondissolved in methylene chloride
  5. washThe solution was washed with sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customCrystallization from methylene chloride/hexane

Sources & evidence

ORD record
ord-a590d9a4939d4f02855eb4a29ab472d7
Source dataset
uspto-grants-1978_09
Patent number
US04111934

Reaction notes

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