Potassium Cyanide → 5-(4-Bromo-3,5-dimethoxyphenyl)-4-tosyl-4,5-dihydrooxazole

HRID 56500Notes

Reaction equation

HRID 56500 reaction equation
[Br:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].[C:14]1([CH3:26])[CH:19]=[CH:18][C:17]([S:20]([CH2:23][N+:24]#[C-:25])(=[O:22])=[O:21])=[CH:16][CH:15]=1.[C-]#N.[K+]>CCO>[Br:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]2[O:7][CH:25]=[N:24][CH:23]2[S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:26])=[CH:15][CH:16]=2)(=[O:22])=[O:21])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 161915Tosylmethyl isocyanideHCID 30155794-Bromo-3,5-dimethoxybenzaldehyde

Product 1

HCID 673894555-(4-Bromo-3,5-dimethoxyphenyl)-4-tosyl-4,5-dihydrooxazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an oven-dried flask under argon was added 4-bromo-3,5-dimethoxybenzaldehyde (1.0 g, 4.08 mmol), absolute EtOH (34 mL), p-toluenesulfonylmethyl isocyanide (0.78 g, 4.0 mmol) and KCN (0.035 g, 0.54 mmol). The mixture was stirred for 19 hours at room temperature then concentrated in vacuo to give 5-(4-bromo-3,5-dimethoxyphenyl)-4-tosyl-4,5-dihydrooxazole which was used in the next synthetic step without purification.

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-082e7c88fd2647c5a12bfb2974dc2338
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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