18-Crown-6 → 2-(3-Fluoro-4-nitrobenzamido)acetic acid

HRID 1399454Notes

Reaction equation

HRID 1399454 reaction equation
[F-:1].[K+].I([C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[C:9]([NH:11][CH2:12][C:13]([O-:15])=[O:14])=[O:10])(=O)=O.[K+].C1OCCOCCOCCOCCOCCOC1>CS(C)=O>[F:1][C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[C:9]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 86713125Potassium 2-(3-iodyl-4-nitrobenzamido)acetate

Product 1

HCID 159257392-(3-Fluoro-4-nitrobenzamido)acetic acidYield 71.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of spray-dried KF (138 mg, 2.3 mmol), intermediate 9 (100 mg, 0.23 mmol), catalytic amount of 18-crown-6 in dry DMSO (4 mL) was stirred at 100-110° C. for 15 min. Work-up of the reaction mixture as described in example 1 gave the product as a colorless solid (40 mg, 69%), mp 136-138° C. 1H NMR (400 MHz, DMSO-d6): δ 8.76 (1H, br s), 8.25 (1H, t, J=7.8 Hz), 8.00 (1H, d, J=12.0 Hz), 7.90 (1H, d, J=8.4 Hz), 3.75 (2H, d, J=4.4 Hz).

Sources & evidence

ORD record
ord-81b4dab56447427b84a581d3ac64b754
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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