4-Aminophenol → HCID 86734104, compound

HRID 1288484Notes

Reaction equation

HRID 1288484 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].O1CCCC1.C(OC(Cl)=O)C(C)C.[CH:27]1[C:32]([NH2:33])=[CH:31][CH:30]=[C:29]([OH:34])[CH:28]=1>O.N1C=CC=CC=1.C(N(CC)CC)C>[C:29]1([OH:34])[CH:30]=[CH:31][CH:32]=[CH:27][CH:28]=1.[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:33])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 4034-AminophenolHCID 8028TetrahydrofuranHCID 19266p-Acetamidobenzoic acidHCID 62365Isobutyl chloroformate

Product 1

HCID 86734104HCID 86734104, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

A solution of p-acetamidobenzoic acid (12.5 g.) in 250 ml. of tetrahydrofuran is treated with triethylamine (11.1 ml.). The mixture is then treated with isobutylchloroformate (10.4 ml.) and, after 5 min. at about 25° C., with p-aminophenol (13.3 g.) in 80 ml. of dry pyridine. After 40 min. the crude product is obtained by addition of 2 liters of water. The product is recrystallized from 500 ml. of hot methanol by dilution with 300 ml. of water as white crystals, 5.9 g., m.p. 275.0°-277.0° C.

Sources & evidence

ORD record
ord-0869283ac2d94c0db657bd0a35caa3e0
Source dataset
uspto-grants-1976_10
Patent number
US03988355

Reaction notes

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