1-Methylimidazole → HCID 178480869, compound

HRID 661602Notes

Reaction equation

HRID 661602 reaction equation
[Cl:1][CH:2]([Cl:27])[C:3]([NH:5][CH:6]([CH2:25][F:26])[CH:7]([O:18][C:19](=[O:24])[CH2:20][CH2:21][CH2:22][Br:23])[C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1)=[O:4].[CH3:28][N:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>O1CCCC1.CCOCC>[Br-:23].[Cl:1][CH:2]([Cl:27])[C:3]([NH:5][CH:6]([CH2:25][F:26])[CH:7]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[O:18][C:19]([CH2:20][CH2:21][CH2:22][N+:31]1[CH:32]=[CH:33][N:29]([CH3:28])[CH:30]=1)=[O:24])=[O:4]

Participants

5

Reactant 2

HCID 13901-MethylimidazoleHCID 57447681HCID 57447681, compound

Product 1

HCID 178480869HCID 178480869, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-butyric acid 2-(2,2-dichloro-acetylamino)-3-fluoro-1-(4-methanesulfonyl-phenyl)-propyl ester (1.8 g, 1 equivalent) and 1-methylimidazol (0.56 mL, 2 equivalents) was stirred in tetrahydrofuran (6 mL) at room temperature overnight. The solution was diluted with ether and the precipitates were collected by filtration and stirred in a mixture of ethyl acetate and hexanes (1:1) at room temperature for 24 hours. The purified title methylimidazolium bromide was collected by filtration and dried under reduced pressure at 50° C. for 7 hours to give a pale powder (1.2 g, 56% yield); H1-NMR (CDCl3/CD3OD). δ=2.2 ppm (m, 2H), 2.6 ppm (m, 2H), 3.0 ppm (s, 3H), 3.9 ppm (s, 3H), 4.2-4.5 ppm (m, 5H), 6.0 ppm (d, 1H), 6.4 ppm (s, 1H), 7.2 ppm (d, 1H), 7.4 ppm (s, 1H), 7.6 (d, 2H), 7.8 ppm (d, 2H), 9.4 ppm (s, 1H).

Workup

  1. filtrationthe precipitates were collected by filtration
  2. customThe purified title methylimidazolium bromide
  3. filtrationwas collected by filtration
  4. customdried under reduced pressure at 50° C. for 7 hours

Sources & evidence

ORD record
ord-8e5e23a9268344968767e01c9ddaefe6
Source dataset
uspto-grants-2011_12
Patent number
US08084643B2

Reaction notes

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