18-Crown-6 → Benzyl 2-(2-fluoro-4-nitrobenzamido)acetate

HRID 1399443Notes

Reaction equation

HRID 1399443 reaction equation
[F-:1].[K+].[N+]([C:6]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:9])([O-])=O.C1OCCOCCOCCOCCOCCOC1>CS(C)=O>[F:1][C:6]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:9]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 86713106Benzyl 2-(2,4-dinitrobenzamido)acetate

Product 1

HCID 86713116Benzyl 2-(2-fluoro-4-nitrobenzamido)acetate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of spray-dried KF (80 mg, 1.392 mmol), intermediate 1 (100 mg, 0.2785 mmol) and catalytic amount of 18-crown-6 in dry DMSO (2 mL) was irradiated using house hold microwave oven for 1.5 min. Work-up of the reaction mixture as described in example 1 (method A) gave benzyl 2-(2-fluoro-4-nitrobenzamido)acetate as a pale yellow color solid (106 mg, 46%), mp 104-106° C. Which was further reduced as described in example 1 gave compound 1.

Workup

  1. customwas irradiated
  2. customfor 1.5 min

Sources & evidence

ORD record
ord-2fb6c72cde214f1aa1087e5cc03f0b2d
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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