Diethyl Ether → 1-[4-(4-{2-[2-(4-Trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazolium methanesulfonat

HRID 1271400Notes

Reaction equation

HRID 1271400 reaction equation
[F:1][C:2]([F:35])([F:34])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]2[O:13][CH:14]=[C:15]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][N:29]4[CH:33]=[CH:32][N:31]=[N:30]4)=[CH:21][CH:20]=3)[N:16]=2)=[CH:6][CH:5]=1.[CH3:36][S:37]([OH:40])(=[O:39])=[O:38].C(OCC)C>O1CCCC1>[CH3:36][S:37]([O-:40])(=[O:39])=[O:38].[F:34][C:2]([F:1])([F:35])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]2[O:13][CH:14]=[C:15]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][NH+:29]4[CH:33]=[CH:32][N:31]=[N:30]4)=[CH:21][CH:20]=3)[N:16]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 694744061-[4-(4-{2-[2-(4-Trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole

Product 1

HCID 865947011-[4-(4-{2-[2-(4-Trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazolium methanesulfonatYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

12.1 g (25 mmol) 1-[4-(4-{2-[2-(4-Trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole were dissolved in 150 ml tetrahydrofuran at 50° C., cooled to room temperature, treated with 1.625 ml (25 mmol) methanesulfonic acid and stirred for lh. After the addition of 300 ml diethyl ether stirring was continued for 1 h, the precipitate collected and washed with diethyl ether. Drying over phosphorus pentoxide yielded 12.4 g (85%) 1-[4-(4-{2-[2-(4-Trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazolium methanesulfonat.

Workup

  1. customthe precipitate collected
  2. washwashed with diethyl ether
  3. dry with materialDrying over phosphorus pentoxide

Sources & evidence

ORD record
ord-a463e4c7289c4c44bc8439ca6e7a5fb2
Source dataset
uspto-grants-2007_04
Patent number
US07205325B2

Reaction notes

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