Acetic Acid → 4-(((5-Chloro-2thienyl)methyl)amino)-benzoic acid

HRID 1701332

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11][C:12]1[S:16][C:15]([CH:17]=O)=[CH:14][CH:13]=1.C(O)(=O)C.CN(B)C>O.C1(C)C=CC=CC=1>[Cl:11][C:12]1[S:16][C:15]([CH2:17][NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture containing 46.6 grams (0.34 moles) of p-aminobenzoic acid, 50 grams (0.34 moles) of 5-chloro-2-thiophenecarboxaldehyde and 400 ml. of toluene was heated to reflux for about three and a half hours. The water formed was collected in a Dean-Stark trap. The reaction mass was cooled at the end of this period and the Schiff base collected as a tan solid. To a mixture of the intermediate Schiff base and 1.2 liters of glacial acetic acid 21.2 grams (0.36 moles) of dimethylaminoborane was added. The reaction mass was warmed to 40° C. for about 30 minutes and poured in 2 liters of ice water. The white precipitate of 4-(((5-chloro-2-thienyl)methyl)amino)benzoic acid was washed in water, dried, and recrystallized from toluene. The melting point was 177°-178° C.

Workup

temperatureto reflux for about three and a half hours
customwas collected in a Dean-Stark trap
temperatureThe reaction mass was cooled at the end of this period
customthe Schiff base collected as a tan solid
additionwas added
customThe reaction
washThe white precipitate of 4-(((5-chloro-2-thienyl)methyl)amino)benzoic acid was washed in water
customdried
customrecrystallized from toluene

Sources & evidence

ORD record: ord-ad488bf1274642eaaa6e1e919907b224
Source dataset: uspto-grants-1980_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04192884

Linked notes

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