Toluene-p-sulphonic anhydride → 2-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl 4-methylbenzenesulfonate

HRID 1157081Notes

Reaction equation

HRID 1157081 reaction equation
[N+:1]([C:4]1[N:5]([CH2:9][C:10]2[N:11]=[N:12][N:13]([CH2:15][CH2:16][OH:17])[CH:14]=2)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[O:18](S(C1C=CC(C)=CC=1)(=O)=O)[S:19]([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=O)=[O:20]>C(Cl)Cl>[CH3:26][C:25]1[CH:27]=[CH:28][C:22]([S:19]([O:17][CH2:16][CH2:15][N:13]2[CH:14]=[C:10]([CH2:9][N:5]3[CH:6]=[CH:7][N:8]=[C:4]3[N+:1]([O-:3])=[O:2])[N:11]=[N:12]2)(=[O:20])=[O:18])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 77773Toluene-p-sulphonic anhydrideHCID 575402032-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethanol

Product 1

HCID 595110572-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl 4-methylbenzenesulfonateYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask containing alcohol 11 (160 mg, 0.672 mmol), TEA (136 mg, 1.34 mmol) and DCM (5 mL) was added Ts2O (263 mg, 0.806 mmol). The reaction was stirred at RT for 4 hrs. TLC indicated that the reaction was complete. The reaction was concentrated in vacuo and purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford 140 mg (53% yield) of 12 as a pale orange oil. Mass Spec (lo-res): Calc'd for C15H16N6O5S: 392.092. found: 393.10 (M+H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified on a silica gel cartridge

Sources & evidence

ORD record
ord-9da76c4d7e15453eb0313362fa643ed5
Source dataset
uspto-grants-2010_10
Patent number
US07807394B2

Reaction notes

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