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

HRID 1461934Notes

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-0dc4ce2c0ec84118bd13303b7ca52038
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05077409

Reaction notes

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