18-Crown-6 → Benzyl 2-(2-fluoro-5-nitrobenzamido)acetate

HRID 1399448Notes

Reaction equation

HRID 1399448 reaction equation
[F-:1].[K+].Cl[C:4]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:5]=1[C:6]([NH:8][CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:7].C1OCCOCCOCCOCCOCCOC1>CS(C)=O>[F:1][C:4]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:5]=1[C:6]([NH:8][CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:7]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 18274893Benzyl 2-(2-chloro-5-nitrobenzamido)acetate

Product 1

HCID 86713120Benzyl 2-(2-fluoro-5-nitrobenzamido)acetateYield 63.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of spray dried KF (208 mg, 3.58 mmol), intermediate 6 (250 mg, 0.71 mmol) and catalytic amount of 18-crown-6 in dry DMSO (5 mL) was stirred at 100-110° C. for 45 min. Work-up of the reaction mixture as described in example 1 gave the product as a brown color solid (150 mg, 63%), mp 56-58° C. 1H NMR (400 MHz, CDCl3): δ 9.00 (1H, dd, J=6.0, 2.8 Hz), 8.36-8.40 (1H, m), 7.31-7.38 (7H, m), 5.25 (2H, s), 4.34 (2H, d, J=4.4 Hz); LC-MS (negative ion mode): m/z 331 (M−H)−.

Sources & evidence

ORD record
ord-16d8903fe8ac4f52bdee5edc083c9c02
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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