2-Amino-2',5-dichlorobenzophenone → 2-Azido-5,2'-dichlorobenzophenone

HRID 267549Notes

Reaction equation

HRID 267549 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=[O:5].N([O-])=O.[Na+].C([O-])(=O)C.[Na+].[N-:27]=[N+:28]=[N-].[Na+]>C(O)(=O)C.Cl.O>[N:1]([C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=[O:5])=[N+:27]=[N-:28]

Participants

8

Reactant 4

HCID 180692-Amino-2',5-dichlorobenzophenoneHCID 33557Sodium AzideHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 215549942-Azido-5,2'-dichlorobenzophenone

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

6,65 G (0.025 mol) of 2-amino-5,2'-dichlorobenzophenone are dissolved in a mixture of 25 ml of glacial acetic acid and 6.25 ml of concentrated hydrochloric acid and diazotised with 5 ml (0.025 mol) of 5 M sodium nitrite solution at 20°C. The mixture is then diluted with 100 ml of ice-cold water and neutralised by addition of 10 g (0.075 mol) of crystalline sodium acetate, and the turbid solution is clarified by filtration, using active charcoal. A solution of 5 g (0.077 mol) of sodium azide in 50 ml of water is added to the filtrate. The reaction product which hereupon precipitates is filtered off and washed with water. After drying over potassium hydroxide and calcium chloride in a desiccator, 2-azido-5,2'-dichlorobenzophenone of decomposition point 100°C is obtained.

Workup

  1. filtrationthe turbid solution is clarified by filtration
  2. customThe reaction product which hereupon precipitates
  3. filtrationis filtered off
  4. washwashed with water
  5. dry with materialAfter drying over potassium hydroxide and calcium chloride in a desiccator

Sources & evidence

ORD record
ord-26d09e0b4f46427e8611c605a7ede29d
Source dataset
uspto-grants-1976_03
Patent number
US03943145

Reaction notes

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