Methyl iodide → 2,6-Diiodo-4-(8-phenyl-octylcarbamoyl)phenyl methyl ether

HRID 1281399Notes

Reaction equation

HRID 1281399 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([C:8](=[O:24])[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=[C:4]([I:25])[C:3]=1[OH:26].[CH3:27]I>>[CH3:27][O:26][C:3]1[C:2]([I:1])=[CH:7][C:6]([C:8](=[O:24])[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:5][C:4]=1[I:25]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 222375592,6-Diiodo-4-(8-phenyloctylcarbamoyl)phenol

Product 1

HCID 222375512,6-Diiodo-4-(8-phenyl-octylcarbamoyl)phenyl methyl ether

Procedure

The title compound was prepared as a solid (0.691 g, 94%) from 2,6-diiodo-4-(8-phenyl-octylcarbamoyl)phenol using methyl iodide and a procedure similar to step 4 of Example 93; 1H NMR (DMSO-d6) δ 1.19-1.34 (m, 8H), 1.41-1.61 (m, 4H), 2.48-2.59 (m, 2H), 3.21 (dd, J=6.4, 14.1 Hz, 2H), 3.78 (s, 3H), 7.10-7.21 (m, 3H), 7.21-7.31 (m 2H), 8.28 (s, 2H), 8.53 (t, J=5.6 Hz, 1H); mass spectrum [(+) ESI], m/z 592 (M+H)+, 614 (M+Na)+.

Sources & evidence

ORD record
ord-94f8439a5d6e4835b05dcb86e695154b
Source dataset
uspto-grants-2002_09
Patent number
US06451827B2

Reaction notes

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