Aspirin → HCID 10424739, compound

HRID 616193Notes

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

Reactant 4

HCID 2244Aspirin

HCID 24386Thionyl Chloride

HCID 796682-Acetoxybenzoyl chloride

HCID 800374-Amino-2,6-dichlorophenol

Product 1

HCID 10424739HCID 10424739, compoundYield 71.1%

Procedure

Acetylsalicylic acid chloride prepared from acetylsalicylic acid and thionyl chloride was condensed with 4-amino-2,6-dichlorophenol followed by deacetylation to yield 3',5'-dichloro-2,4'-dihydroxybenzanilide (4 g.).

Sources & evidence

ORD record: ord-e6e68c01c6314ee7810acffb27bed9d3
Source dataset: uspto-grants-1978_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04072753

Reaction notes

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