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

HRID 484627Notes

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-a704655bde7e47698184081bf4f2040f
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05231182

Reaction notes

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