Iron → Fe Ac2O AcOH

HRID 1399456Notes

Reaction equation

HRID 1399456 reaction equation
[F-].[K+].I(C1C=C(C=CC=1[N+]([O-])=O)C(N[CH2:12][C:13]([O-:15])=[O:14])=O)(=O)=O.[K+].[CH2:23]1OCCOCCOCCOCCOCC[O:25][CH2:24]1.[Fe:41]>CS(C)=O.CC(O)=O.CC(OC(C)=O)=O>[Fe:41].[CH3:23][C:24]([O:15][C:13]([CH3:12])=[O:14])=[O:25].[CH3:12][C:13]([OH:15])=[O:14]

Participants

8

Reactant 4

HCID 23925IronHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 86713125Potassium 2-(3-iodyl-4-nitrobenzamido)acetate

Product 1

HCID 86713117Fe Ac2O AcOHYield 236.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of spray-dried KF (138 mg, 2.3 mmol), intermediate 9 (100 mg, 0.23 mmol) and catalytic amount of 18-crown-6 (20 mg) 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 residue. This residue was dissolved in a mixture of AcOH and Ac2O (5 mL, 1:1) and added iron powder (193 mg, 3.44 mmol) at rt. The mixture was stirred at 85-90° C. for 15 min and work-up of the reaction mixture as described in example 2 gave the product as an off-white color solid (39 mg, 65%), mp 236-238° C.; 1H NMR (400 MHz, DMSO-d6): δ 12.53 (1H, br s), 9.92 (1H, br s), 8.84 (1H, t, J=6 Hz), 8.11 (1H, t, J=7.6 Hz), 7.67-7.73 (2H, m), 3.92 (2H, d, J=5.2 Hz), 2.13 (3H, s); LC-MS (negative ion mode): m/z 253 (M−H)−.

Workup

  1. customgave the residue
  2. stirringThe mixture was stirred at 85-90° C. for 15 min

Sources & evidence

ORD record
ord-7defa1c5f73c4aa89b88e186c6dc4cc9
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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