3-Nitrobenzaldehyde → 5-(3-Nitrophenyl)oxazole

HRID 1753776Notes

Reaction equation

HRID 1753776 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].CC1C=CC(S([CH2:22][N+:23]#[C-:24])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]2[O:8][CH:24]=[N:23][CH:22]=2)[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanide

Product 1

HCID 27370675-(3-Nitrophenyl)oxazoleYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate X-a was prepared as for example I-c using 3-nitrobenzaldehyde (4 g, 26 mmol), TosMIC (5.7 g, 29 mmol) and K2CO3 (4.4 g, 32 mmol) in MeOH to give intermediate X-a as a yellow solid (4.7 g, 93%). 1H NMR (400 MHz, DMSO-d6) δ 8.56 (s, 1H), 8.50 (t, J=1.9 Hz, 1H), 8.21 (ddd, J=8.2, 2.3, 1.0 Hz, 1H), 8.17 (ddd, J=7.8, 1.6, 1.0 Hz, 1H), 7.99 (s, 1H), 7.78 (t, J=8.0 Hz, 1H).

Sources & evidence

ORD record
ord-03ca4f1c7b82474f866420a19d76c008
Source dataset
uspto-grants-2015_10
Patent number
US09168245B2

Reaction notes

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