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

HRID 2163815Notes

Reaction equation

HRID 2163815 reaction equation
[N:1]([O-:3])=O.[Na+].[Cl:5][C:6]1[CH:25]=[CH:24][C:9]2[N:10]=[C:11]([NH:22][CH3:23])[CH2:12][C:13](=[O:21])[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:7]=1.O>C(O)(=O)C>[Cl:5][C:6]1[CH:25]=[CH:24][C:9]2[N:10]=[C:11]([NH:22][CH2:23][N:1]=[O:3])[CH2:12][C:13](=[O:21])[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 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 176Acetic AcidSolvent

Procedure

Sodium nitrite, 21.26 g (0.308 m) was added over a period of 20 min to a stirred solution of 71 g (0.237 m) of 7-chloro-3,5-dihydro-2-methylamino-5-phenyl-4H-1,5-benzodiazepin-4-one in 500 ml of acetic acid. Following the addition, the mixture was stirred for 1 hr at room temperature and was then diluted with 1.5 l. of water. The precipitated product was collected, washed with water and dissolved in methylene chloride. The solution was washed with saturated sodium bicarbonate solution, dried over sodium sulfate and evaporated. The residue was crystallized from ether to yield yellow crystals with mp 121°-124°. A second crop was obtained from the mother liquor.

Workup

  1. additionthe addition
  2. additionwas then diluted with 1.5 l
  3. customThe precipitated product was collected
  4. washwashed with water
  5. dissolutiondissolved in methylene chloride
  6. washThe solution was washed with saturated sodium bicarbonate solution
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue was crystallized from ether
  10. customto yield yellow crystals with mp 121°-124°
  11. customA second crop was obtained from the mother liquor

Sources & evidence

ORD record
ord-d7ec5b14821b49818e32b78adccc3e44
Source dataset
uspto-grants-1979_01
Patent number
US04137229

Reaction notes

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