Methyl Chloride → HCID 178443025, compound

HRID 1706383Notes

Reaction equation

[CH2:1]([N:17]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[N:18]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][CH2:14][CH2:15][CH3:16].[CH3:24][Cl:25]>S1(CCCC1)(=O)=O>[Cl-:25].[CH2:1]([N+:17]1[N:18]([CH3:24])[C:19]([CH3:23])=[CH:20][C:21]=1[CH3:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: -40 °C

Procedure

A mixture of 16. g (0.05 mol) of 1-hexadecyl-3,5-dimethylpyrazole and 50 ml of sulfolane is cooled down to -30° C. in a rotary autoclave and 9 g (0.18 mol) of liquid methyl-chloride cooled down to -40° C. are added. Upon sealing the autoclave, the reaction mixture is heated to 120° C. and kept at this temperature for 60 hrs. After cooling, the sulfolane is distilled off under high vacuum. 50 Ml of ether are added to the residue and the mixture shaken thoroughly. The crystalate is then filtered off and recrystallized first from 100 ml of acetone and then from 60 ml of acetone, filtered off, and vacuum dried at 40° C./12 Torr to yield about 10.1 g of 1-hexadecyl-2,3,5-trimethyl-pyrazolium chloride; m.p. 92°-94° C. The same compound is obtained by appropriate anion exchange of the product obtained in Example I.

Workup

additionare added
temperaturethe reaction mixture is heated to 120° C.
temperatureAfter cooling
distillationthe sulfolane is distilled off under high vacuum
addition50 Ml of ether are added to the residue
filtrationThe crystalate is then filtered off
customrecrystallized first from 100 ml of acetone
filtrationfrom 60 ml of acetone, filtered off
customvacuum dried at 40° C./12 Torr

Sources & evidence

ORD record: ord-4e4526680e38409489b3278a52c76f51
Source dataset: uspto-grants-1980_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04207326

Reaction notes

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