Aniline → 4-(2-Oxazolyl)-3-chloroaniline

HRID 964627Notes

Reaction equation

HRID 964627 reaction equation
ClC1C=C(C=CC=1[N+]([O-])=O)C(Cl)=O.N1C=CN=N1.C([O-])([O-])=O.[K+].[K+].[Cl:25][C:26]1[CH:27]=[C:28]([N+:37]([O-])=O)[CH:29]=[CH:30][C:31]=1[C:32]1[O:33][CH:34]=[CH:35][N:36]=1.NC1C=CC=CC=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>S1(CCCC1)(=O)=O.C1COCC1.O>[O:33]1[CH:34]=[CH:35][N:36]=[C:32]1[C:31]1[CH:30]=[CH:29][C:28]([NH2:37])=[CH:27][C:26]=1[Cl:25]

Participants

9

Reactant 6

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 190776143-Chloro-4-nitrobenzoyl chlorideHCID 190776273-Chloro-4-(2-oxazolyl)nitrobenzeneHCID 178418936HCID 178418936, compound

Product 1

HCID 190776084-(2-Oxazolyl)-3-chloroaniline

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-chloro-4-(2-oxazolyl)aniline to generate the title compound. The 4-(2-oxazolyl)-3-chloroaniline was prepared by treating commercial 3-chloro-4-nitrobenzoyl chloride sequentially with 1,2,3-triazole at 140° C. in sulfolane containing K2CO3 to generate 3-chloro-4-(2-oxazolyl)nitrobenzene which was reduced to the desired aniline with Na2S2O4 in THF/H2O at 90° C.

Sources & evidence

ORD record
ord-5c9ce98018814d338ecb19d751d84dfc
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

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