Diethyl Ether → 3-Methyl-2-[[3-[acetyl[2-[4-(tetradecyloxy)phenyl]ethyl]amino]phenyl]methyl]thiazolium iodide

HRID 2227084Notes

Reaction equation

[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][N:24]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][C:35]3[S:36][CH:37]=[CH:38][N:39]=3)[CH:29]=2)[C:25](=[O:27])[CH3:26])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C[I:41].[CH3:42]COCC>C1(C)C=CC=CC=1>[I-:41].[CH3:42][N+:39]1[CH:38]=[CH:37][S:36][C:35]=1[CH2:34][C:30]1[CH:31]=[CH:32][CH:33]=[C:28]([N:24]([C:25](=[O:27])[CH3:26])[CH2:23][CH2:22][C:19]2[CH:18]=[CH:17][C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:21][CH:20]=2)[CH:29]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 300 mg of N-[2-[4-(tetradecyloxy)phenyl]ethyl]-N-[3-(2-thiazolylmethyl)phenyl]acetamide and 1.4 g of methyl iodide in 5 ml of toluene is heated at 140° C. in a closed vessel for 4.5 hours then cooled. Ether is added, the solid collected by centrifugation and then washed several times with ether. The solid is vacuum dried to give 235 mg of the desired product as a tan solid, m.p. 130°-134° C.

Workup

temperaturethen cooled
customthe solid collected by centrifugation
washwashed several times with ether
customdried

Sources & evidence

ORD record: ord-d37b30c9df034d45bd266e871cc6c3ba
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05350759

Reaction notes

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