18-Crown-6 → Benzyl 2-(4-fluoro-3-nitrobenzamido)acetate

HRID 1399445Notes

Reaction equation

HRID 1399445 reaction equation
[F-:1].[K+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][C:25]=1[N+]([O-])=O)[C:9]([NH:11][CH2:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[O:10])([O-:5])=[O:4].C1OCCOCCOCCOCCOCCOC1>CS(C)=O>[F:1][C:25]1[CH:24]=[CH:23][C:8]([C:9]([NH:11][CH2:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[O:10])=[CH:7][C:6]=1[N+:3]([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 86713107Benzyl 2-(3,4-dinitrobenzamido)acetate

Product 1

HCID 86713118Benzyl 2-(4-fluoro-3-nitrobenzamido)acetateYield 56.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of spray-dried KF (80 mg, 1.39 mmol), intermediate 3 (100 mg, 0.27 mmol) and catalytic amount of 18-crown-6 in dry DMSO (4 mL) was stirred at 110-120° C. for 10 min. Work-up of the reaction mixture as described in example 1 gave the product as a pale yellow color solid (51 mg, 55%), mp 84-86° C. 1H NMR (400 MHz, CDCl3): δ 8.50 (1H, dd, J=6.8, 1.6 Hz), 8.10-8.13 (1H, m), 7.34-7.39 (6H, m), 6.90 (1H, br s), 5.23 (2H, s), 4.28 (2H, d, J=5.2 Hz); LC-MS (negative ion mode): m/z 331 (M−H)−.

Sources & evidence

ORD record
ord-34add74725cc4220a2bb5ff34b98901a
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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