Ethanol → Methyl 2-(5-methylbenzoxazol-2-yl)benzoate

HRID 273744Notes

Reaction equation

[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[CH:3]=1.[CH:10]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#N)=[O:11].[CH2:20]([OH:22])C>>[CH3:9][C:4]1[CH:5]=[CH:6][C:7]2[O:8][C:14]([C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[C:10]([O:22][CH3:20])=[O:11])=[N:1][C:2]=2[CH:3]=1

Participants

Reactant 3

HCID 702Ethanol

HCID 72642-Amino-4-methylphenol

HCID 1012092-Cyanobenzaldehyde

Product 1

HCID 20094237Methyl 2-(5-methylbenzoxazol-2-yl)benzoate

Procedure

A solution of 2-amino-p-cresol (9.8 g) and 2-formylbenzonitrile (10.5 g) in ethanol (160 ml) was allowed to stand for 20 hours. The precipitated solid was filtered off and washed with ethanol (30 ml) to give 2-hydroxy-5-methyl-N-(2-cyanobenzylidene)aniline (C) (3.1 g), m.p. 135°-138° C.; NMR: 2.35(s, 3H), 6.95(d, 1H), 7.1(dd, 1H), 7.2(s & br s, 2H), 7.55(dt, 1H), 7.7(dt, 1H), 7.8(dd, 1H) 8.1(dd, 1H), 8.9(s, 1H).

Workup

filtrationThe precipitated solid was filtered off
washwashed with ethanol (30 ml)

Sources & evidence

ORD record: ord-fedf5bc000f243f1b3435852131f5c5c
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05387592

Reaction notes

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