Potassium Iodide → HCID 22506194, compound

HRID 1814435Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:28]1([NH:34][C:35]([NH:37][CH2:38][CH2:39][CH2:40]Br)=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CC#N.CN(C=O)C>[C:28]1([NH:34][C:35](=[O:36])[NH:37][CH2:38][CH2:39][CH2:40][N:10]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of bis[2-(4-chlorophenyl)ethyl]amine (48 mg, 0.16 mmol), potassium carbonate (44 mg, 0.32 mmol) and potassium iodide (26 mg, 0.16 mmol) in CH3CN (2 ml) was added N-phenylcarbamoyl-3-bromopropylamine (215 mg, 0.64 mmol) in DMF (2 ml). The mixture was stirred at 80° C. for 18 h, and then concentrated under vacuum to dryness. The residue was adsorbed on a plate of silica gel and then developed with 10% methanol/chloroform to afford [3-(phenylureido)propyl]bis[2-(4-chlorophenyl)ethyl]amine (10 mg, 13%): MS(ES+) m/e 470 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 7.24 (m, 9H), 7.03 (m, 5H), 6.59 (br, 1H), 3.24 (t, J=6.3 Hz, 2H), 2.87 (m, 1H), 2.76 (m, 1H), 2.73-2.61 (m, 8H), 1.64 (m, 2H).

Workup

concentrationconcentrated under vacuum to dryness

Sources & evidence

ORD record: ord-317d45f2a335402f9a87ee51eb64c53b
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875884B1

Reaction notes

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