Sodium Hydroxide → HCID 20323116, compound

HRID 1973626Notes

Reaction equation

HRID 1973626 reaction equation
C[N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5][CH2:4][CH:3]1[CH2:19][Cl:20].[N+:21]([O-])([O-:23])=[O:22].[K+].[OH-].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O>[ClH:20].[N+:21]([C:11]1[CH:10]=[CH:9][C:8]2[NH:2][CH:3]([CH2:19][Cl:20])[CH2:4][N:5]=[C:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]=2[CH:12]=1)([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 12923439HCID 12923439, compound

Product 1

HCID 20323116HCID 20323116, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 3.7 g of 1-methyl-2-chloromethyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine in 20 ml glacial acetic acid and 6 ml concentrated sulfuric acid were reacted at 5° C with a solution of 3.2 g potassium nitrate in 7 ml concentrated sulfuric acid. The reaction mixture was stirred for 1 hour at room temperature, then poured onto ice, made alkaline with dilute sodium hydroxide and extracted with chloroform. The several chloroform extracts were dried and concentrated by evaporation in a vacuum. The residual oil was dissolved in isopropanol and reacted with an ether solution of hydrogen chloride. There were obtained 7-nitro-2-chloromethyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine hydrochloride; m.p. 213° - 214° C.

Workup

  1. additionpoured onto ice
  2. extractionextracted with chloroform
  3. dry with materialThe several chloroform extracts were dried
  4. concentrationconcentrated by evaporation in a vacuum
  5. dissolutionThe residual oil was dissolved in isopropanol
  6. customreacted with an ether solution of hydrogen chloride

Sources & evidence

ORD record
ord-5bf9f5baf21e41f2b19f46e432e98ca5
Source dataset
uspto-grants-1976_12
Patent number
US03998809

Reaction notes

Loading…