4-Nitrobenzoic Acid → 1-(p-Nitrobenzoyloxy)-6-chloro-1,2,3-benzotriazole

HRID 1733676Notes

Reaction equation

HRID 1733676 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.ClC1C=CC(S(O[N:31]2[C:35]3[CH:36]=[C:37]([Cl:40])[CH:38]=[CH:39][C:34]=3[N:33]=[N:32]2)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][N:31]2[C:35]3[CH:36]=[C:37]([Cl:40])[CH:38]=[CH:39][C:34]=3[N:33]=[N:32]2)=[O:9])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 8471TriethylamineHCID 122228411-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole

Product 1

HCID 203000071-(p-Nitrobenzoyloxy)-6-chloro-1,2,3-benzotriazoleYield 75.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

p-Nitrobenzoic acid (1.67 g) is dissolved in chloroform (20 ml) and thereto are added triethylamine (1.40 ml) under ice-cooling and further 1-(p-chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole (3.44 g) at room temperature. When the mixture is stirred at room temperature for 20 minutes, white crystals precipitate, and the mixture is further stirred for 7 hours. The precipitated crystals are separated by filtration to give white crystals of 1-(p-nitrobenzoyloxy)-6-chloro-1,2,3-benzotriazole (2.4 g), melting point: 198°-199° C. (decomp).

Workup

  1. temperaturecooling
  2. customat room temperature
  3. stirringwhite crystals precipitate, and the mixture is further stirred for 7 hours
  4. customThe precipitated crystals are separated by filtration

Sources & evidence

ORD record
ord-1d650dacc15449fa92794e18748b6315
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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