Aspirin → HCID 10424739, compound
Reaction equation
C([O:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:7](Cl)=[O:8])(=O)C.C(OC1C(=CC=CC=1)C(O)=O)(=O)C.S(Cl)(Cl)=O.[NH2:31][C:32]1[CH:37]=[C:36]([Cl:38])[C:35]([OH:39])=[C:34]([Cl:40])[CH:33]=1>>[Cl:38][C:36]1[CH:37]=[C:32]([CH:33]=[C:34]([Cl:40])[C:35]=1[OH:39])[NH:31][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=1[OH:4]Participants
5
Procedure
Acetylsalicyloyl chloride prepared by reaction of acetylsalicylic acid with thionyl chloride was condensed with 4-amino-2,6-dichlorophenol, and then deacetylated to give 3',5'-dichloro-2,4'-dihydroxybenzanilide. That compound (4 g.) was dissolved in cold anhydrous acetic acid (50 ml.) and with stirring there was added with 3 drops of concentrated sulfuric acid. After reaction for 1-2 hours at 5°-6° C., the solution was poured into ice-cold water (500 ml.) and the white precipitate thus formed was collected by filtration, rinsed with water, dried and recrystallized from methanol to give white needle-like crystals (3.65 g.) of 2,4'-diacetoxy-3',5'-dichlorobenzanilide. Yield: 71.1%. Melting point: 154°-156° C.
Sources & evidence
- ORD record
- ord-143929e1bf5041d7a3901ddf0c8fae8d
- Source dataset
- uspto-grants-1976_08
- Patent number
- US03973038
Reaction notes
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