Sodium Nitrite → HCID 178526918, compound

HRID 1413334Notes

Reaction equation

HRID 1413334 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[CH:12][N+:13]([O-:15])=[O:14])[CH2:9][N+:8]([O-:16])=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[C:6]=2[CH:24]=1.[N:25]([O-])=[O:26].[Na+]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([C:12]([N+:13]([O-:15])=[O:14])=[N:25][OH:26])[CH2:9][N+:8]([O-:16])=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[C:6]=2[CH:24]=1

Participants

5

Reactant 2

HCID 23668193Sodium Nitrite2×HCID 178526910HCID 178526910, compound

Product 1

HCID 178526918HCID 178526918, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2-nitromethylene-2H-1,4-benzodiazepine-4-oxide* 7 g (0.02 mole), was dissolved by heating in 250 ml of glacial acetic acid. The solution was cooled with tap water and when the temperature reached 70° C. the addition of 1.9 g (0.0275 mole) of sodium nitrite was started. The sodium nitrite was added over a period of 10 min while cooling was continued. Following the addition, the mixture was stirred for 11/2 hr at room temperature, diluted with water and extracted with methylene chloride. The extracts were washed with water, dried over sodium sulfate and evaporated. Crystallization of the residue from ethyl acetate yielded yellow crystals. The analytical sample was recrystallized from methanol/ethyl acetate to give yellow crystals with undefined mp. The compound decomposes without prior melting.

Workup

  1. dissolutionwas dissolved
  2. customreached 70° C.
  3. temperaturewhile cooling
  4. additionthe addition
  5. extractionextracted with methylene chloride
  6. washThe extracts were washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customCrystallization of the residue from ethyl acetate yielded yellow crystals
  10. customThe analytical sample was recrystallized from methanol/ethyl acetate
  11. customto give yellow crystals with undefined mp. The compound

Sources & evidence

ORD record
ord-b25279ffb399497d9740c74475c0c102
Source dataset
uspto-grants-1981_02
Patent number
US04250095

Reaction notes

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