Aniline → 3-(1,3-Oxazol-2-yl)aniline

HRID 964626Notes

Reaction equation

HRID 964626 reaction equation
[N+](C1C=C(C=CC=1)C(Cl)=O)([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:30]=[C:31]([N+:35]([O-])=O)[CH:32]=[CH:33][CH:34]=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:30]=[C:31]([CH:32]=[CH:33][CH:34]=1)[NH2:35]

Participants

9

Reactant 6

HCID 6115AnilineHCID 8495Benzoyl chloride, 3-nitro-HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 12371737HCID 12371737, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 123717413-(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 3-(2-oxazolyl)aniline to generate the title compound. The 3-(2-oxazolyl)aniline was prepared by treating 3-nitrobenzoyl chloride sequentially with 1,2,3-triazole at 140° C. in sulfolane containing K2CO3 to generate 3-(2-oxazolyl)nitrobenzene which was reduced to the desired aniline with Na2S2O4 in THF/H2O at 90° C.

Sources & evidence

ORD record
ord-10f93cd1ac6547b0b6abde98cc9d2a53
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

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