Monobenzone → 3-(4-Benzyloxyphenoxy)-7-chloro-1,2,4-benzotriazine-1-oxide

HRID 1164163Notes

Reaction equation

HRID 1164163 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl[C:21]1[N:22]=[N+:23]([O-:32])[C:24]2[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:25]=2[N:26]=1>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:21]2[N:22]=[N+:23]([O-:32])[C:24]3[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:25]=3[N:26]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7638MonobenzoneHCID 24758Sodium hydrideHCID 130939893,7-Dichloro-1-oxo-1lambda~5~,2,4-benzotriazineHCID 178418361HCID 178418361, compound

Product 1

HCID 205125803-(4-Benzyloxyphenoxy)-7-chloro-1,2,4-benzotriazine-1-oxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
125 °C

Procedure

In a nitrogen atmosphere, a solution of 0.1 mole 4-benzyloxyphenol in 50 cc dimethylformamide is added dropwise at about 15° C. to 0.1 mole 57% sodium hydride in 25 cc dimethylformamide. When evolution of hydrogen ceases, 0.1 mole 3,7-dichloro-1,2,4-benzotriazine-1-oxide is added and the reaction mixture is heated at 125° C. for about 2 hours. After standing overnight at room temperature, the reaction mixture is poured into ice-water (~500 cc). The solid product is filtered and crystallized from methanol or acetonitrile.

Workup

  1. filtrationThe solid product is filtered
  2. customcrystallized from methanol or acetonitrile

Sources & evidence

ORD record
ord-f1c599e5cbc448e687d9d40775258757
Source dataset
uspto-grants-1983_01
Patent number
US04368068

Reaction notes

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