Triethylamine → 1-[2-[4-[(Methylsulfonyl)amino]phenyl]ethyl]-1H-imidazole

HRID 1789479Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1)(=[O:25])=[O:24]

Participants

Conditions

Temperature: -10 °C

Procedure

To a -10° C. solution of 8 g (0.064 mole) of 1-[2-(4-aminophenyl)ethyl]-1H-imidazole and 10 mL triethylamine in 200 mL of methylene chloride add 5 mL of methanesulfonyl chloride dropwise. Stir the resulting solution at -10° C. for about 30 minutes then warm to ambient temperature for about 30 minutes. Wash the reaction mixture with water (2×100 mL). Extract with 10% aqueous sodium hydroxide (2×50 mL). The combined aqueous extracts are neutralized with ammonium chloride then extracted with methylene chloride (2×100 mL) and combined. Remove the solvent in vacuo to provide the title compound, which may be recrystallized from tetrahydrofuran.

Workup

temperaturethen warm to ambient temperature for about 30 minutes
washWash the reaction mixture with water (2×100 mL)
extractionExtract with 10% aqueous sodium hydroxide (2×50 mL)
extractionthen extracted with methylene chloride (2×100 mL)
customRemove the solvent in vacuo

Sources & evidence

ORD record: ord-cd66aca946ca4ec298c6a1d5a5a8d280
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04689341

Reaction notes

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