Acetic Anhydride → 2-Chloro-6-cyano-4-(3-fluorosulfonylphenylazo)phenyl acetate

HRID 263151Notes

Reaction equation

[Cl:1][C:2]1[C:3]([OH:23])=[C:4]([CH:8]=[C:9]([N:11]=[N:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([F:22])(=[O:21])=[O:20])[CH:14]=2)[CH:10]=1)[CH:5]=[N:6]O.[C:24](OC(=O)C)(=[O:26])[CH3:25].C([O-])(=O)C.[Na+]>O>[C:24]([O:23][C:3]1[C:4]([C:5]#[N:6])=[CH:8][C:9]([N:11]=[N:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([F:22])(=[O:21])=[O:20])[CH:14]=2)=[CH:10][C:2]=1[Cl:1])(=[O:26])[CH3:25]

Participants

Conditions

Temperature: 95 °C

Procedure

3-Chloro-5-(3-fluorosulfonylphenylazo)-2-hydroxybenzaldehyde oxime (22.5 g, 0.063 mol) was added to 150 ml acetic anhydride and heated to 95° C. Sodium acetate (3.0 g) was added. After 21/2 hours, the reaction mixture was poured into 750 ml water and stirred at room temperature until anhydride fully hydrolysed. The resulting precipitate was filtered off. The solids which became gummy on standing were dissolved in 75 ml chloroform and poured onto a silica gel column. Elution with 10% hexane in chloroform gave the desired dye as the first component. Removal of the solvents under reduced pressure gave an oil which hardened on standing but did not crystallize. Yield: 16.8 g (70%).

Workup

filtrationThe resulting precipitate was filtered off
dissolutionon standing were dissolved in 75 ml chloroform
additionpoured onto a silica gel column
washElution with 10% hexane in chloroform
customgave the desired dye as the first component
customRemoval of the solvents under reduced pressure
customgave an oil which
customdid not crystallize

Sources & evidence

ORD record: ord-078c782d6ac345aca44b934ef6417c84
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04156609

Reaction notes

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