Aniline → 4-(1,3-Oxazol-2-yl)aniline

HRID 964625Notes

Reaction equation

HRID 964625 reaction equation
[N+](C1C=CC(C(Cl)=O)=CC=1)([O-])=O.N1C=CN=N1.C([O-])([O-])=O.[K+].[K+].[O:24]1[CH:28]=[CH:27][N:26]=[C:25]1[C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[CH:31][CH:30]=1.NC1C=CC=CC=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>S1(CCCC1)(=O)=O.C1COCC1.O>[O:24]1[CH:28]=[CH:27][N:26]=[C:25]1[C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=1

Participants

9

Reactant 6

HCID 6115AnilineHCID 85024-Nitrobenzoyl chlorideHCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 109762762-(4-Nitrophenyl)oxazoleHCID 178418936HCID 178418936, compound

Product 1

HCID 123717394-(1,3-Oxazol-2-yl)aniline

Reagents, catalysts & solvents 2

HCID 31347SulfolaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Following the procedure described in part E of Example 1 (R), (S)-α-[[2-[((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxybenzeneacetic acid was condensed with 4-(2-oxazolyl)aniline to generate the title compound. The 4-(2-oxazolyl)aniline was prepared by treating 4-nitrobenzoyl chloride sequentially with 1,2,3-triazole at 140° C. in sulfolane containing K2CO3 to generate 4-(2-oxazolyl)nitrobenzene which was reduced to the desired aniline with Na2S2O4 in THF/H2O at 90° C.

Sources & evidence

ORD record
ord-e1fc985bc04b42a293e46232a10776ea
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

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