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

HRID 964628Notes

Reaction equation

HRID 964628 reaction equation
ClC1C=CC(C(Cl)=O)=CC=1[N+]([O-])=O.N1C=CN=N1.C([O-])([O-])=O.[K+].[K+].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][C:27]=1[C:35]1[O:36][CH:37]=[CH:38][N:39]=1.NC1C=CC=CC=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>S1(CCCC1)(=O)=O.C1COCC1.O>[O:36]1[CH:37]=[CH:38][N:39]=[C:35]1[C:27]1[CH:28]=[C:29]([CH:30]=[CH:31][C:26]=1[Cl:25])[NH2:32]

Participants

9

Reactant 6

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 1234774-Chloro-3-nitrobenzoyl chlorideHCID 190776092-(2-Chloro-5-nitrophenyl)oxazoleHCID 178418936HCID 178418936, compound

Product 1

HCID 190775943-(2-Oxazolyl)-4-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-[[[-((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxybenzeneacetic acid was condensed with 3-(2-oxazolyl)-4-chloroaniline to generate the title compound. The 3-(2-oxazolyl)-4-chloroaniline was prepared by treating commercial 4-chloro-3-nitrobenzoyl chloride sequentially with 1,2,3-triazole at 140° C. in sulfolane containing K2CO3 to generate 4-chloro-3-(2-oxazolyl)nitrobenzene which was reduced to the desired aniline with Na2S2O4 in THF/H2O at 90° C.

Sources & evidence

ORD record
ord-f1feceba5cad4f4d8f6f28f5d2598196
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

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