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

HRID 1399452Notes

Reaction equation

HRID 1399452 reaction equation
[F-:1].[K+].I([C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[C:9]([NH:11][CH2:12][C:13]([O:15][CH2:16][C:17]([Cl:20])([Cl:19])[Cl:18])=[O:14])=[O:10])(=O)=O.C1OCCOCCOCCOCCOCCOC1>CS(C)=O>[F:1][C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[C:9]([NH:11][CH2:12][C:13]([O:15][CH2:16][C:17]([Cl:20])([Cl:19])[Cl:18])=[O:14])=[O:10]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 867131132,2,2-Trichloroethyl 2-(3-iodyl-4-nitrobenzamido)acetate

Product 1

HCID 867131242,2,2-Trichloroethyl 2-(3-fluoro-4-nitrobenzamido)acetateYield 66.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
97.5 °C

Procedure

A mixture of spray-dried KF (135 mg, 2.3 mmol), intermediate 8 (120 mg, 0.23 mmol) and catalytic amount of 18-crown-6 in DMSO (5 mL) was stirred at 95-100° C. for 15 min. Work-up of the reaction mixture as described in example 1 gave the product as a yellow color solid (57 mg, 65%), mp 142-144° C. 1H NMR (400 MHz, CDCl3): δ 8.15 (1H, t, J=7.8 Hz), 7.78 (1H, dd, J=10.8, 1.6 Hz), 7.71 (1H, d, J=8.4 Hz), 6.70 (1H, br s), 4.86 (2H, s), 4.44 (2H, d, J=5.2 Hz); LC-MS (negative ion mode): m/z 371, 373 (M−H)−.

Sources & evidence

ORD record
ord-74b5ab7619c14858b8d5df17d6e48377
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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