Triethylamine → HCID 86620170, compound

HRID 1930428Notes

Reaction equation

HRID 1930428 reaction equation
[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C(N(CC)CC)C.[S:20](Cl)([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21].CCOC(C)=O>C(Cl)Cl>[F:24][C:23]([F:26])([F:25])[S:20]([O:12][C:9]1[CH:10]=[CH:11][C:6]([C:2]2[O:1][CH:5]=[N:4][N:3]=2)=[CH:7][CH:8]=1)(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 79000Trifluoromethanesulfonyl chlorideHCID 7147704-(1,3,4-Oxadiazol-2-yl)phenol

Product 1

HCID 86620170HCID 86620170, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-(1,3,4-oxadiazol-2-yl)phenol (1.05 g, 6.48 mmol) and triethylamine (1.82 mL, 13.0 mmol) in CH2Cl2 (12 mL) was cooled to 0° C. and treated with triflic chloride (0.83 mL, 7.77 mmol). The resultant orange-colored reaction was stirred 30 min at 0° C. and 30 min at RT. The reaction was poured into EtOAc (50 mL), washed with water (20 mL), satd aq NaHCO3 (20 mL) and brine (20 mL), dried (Na2SO4) and concentrated in vacuo to provide 4-(1,3,4-Oxadiazol-2-yl)phenyl trifluoromethanesulfonate (1.94 g, 102% yield) as a beige-colored solid. 1H NMR (400 MHz, DMSO-d6): δ 9.43 (s, 1 H), 8.22 (d, J=8.6 Hz, 2 H), 7.78 (d, J=8.6 Hz, 2 H).

Workup

  1. customThe resultant orange-colored reaction
  2. washwashed with water (20 mL), satd aq NaHCO3 (20 mL) and brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-66cc61541c0a45e6ba7f7f197255d84c
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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