Potassium Iodide → HCID 11537354, compound

HRID 905596Notes

Reaction equation

HRID 905596 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10](=[O:17])[CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:4]([Cl:18])[CH:3]=1.Cl[CH2:20][CH2:21][O:22][CH2:23][CH2:24]Cl.[I-].[K+]>C(O)C>[Cl:18][C:4]1[CH:3]=[C:2]([N:1]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:7]=[C:6]([CH3:8])[C:5]=1[NH:9][C:10](=[O:17])[CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8115Bis(2-chloroethyl) etherHCID 67407530HCID 67407530, compound

Product 1

HCID 11537354HCID 11537354, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
170 °C

Procedure

N-(4-Amino-2-chloro-6-methyl-phenyl)-2-cyclopentyl-acetamide (830 mg), bis-(2-chloroethyl)ether (3.35 mL) and potassium iodide (470 mg) were mixed in absolute ethanol (33 mL) and heated to 170° C. for 1 hour in a sealed microwave process vial. The crude mixture was concentrated in mow and purified by flash chromatography to furnish 390 mg (41%) of the title compound as a white solid. LC-MS (m/z) 337 (MH+); tR=2.61, (UV, ELSD) 97%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.22 (m, 2H), 1.51 (m, 2H), 1.61 (m, 2H), 1.77 (m, 2H), 2.11 (s, 3H), 2.25 (m, 1H), 2.26 (m, 2H), 3.10 (m, 4H), 3.71 (m, 4H), 6.80 (d, 1H), 6.84 (d, 1H), 9.18 (s,

Workup

  1. concentrationThe crude mixture was concentrated in mow
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-0152151faca041b0b6d935fa00a7a5dd
Source dataset
uspto-grants-2011_09
Patent number
US08012962B2

Reaction notes

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