Triethylamine → HCID 57655938, compound

HRID 2041571Notes

Reaction equation

HRID 2041571 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=2)=[O:8])[CH:2]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[CH3:24][S:25]([O:14][CH2:13][C:12]1[CH:11]=[CH:10][C:9]([C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:8])=[CH:16][CH:15]=1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 184620204-(Pyridine-3-carbonyl)-benzyl alcohol

Product 1

HCID 57655938HCID 57655938, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve 4-(pyridine-3-carbonyl)-benzyl alcohol (85 mg, 0.399 mmol) in dichloromethane (5 mL). Cool to 0° C. and add triethylamine (0.056 mL, 0.438 mmol) and methanesulfonyl chloride (0.033 mL, 0.438 mmol). Allow the mixture to warm to room temperature and stir for 2 h. Dilute the reaction mixture with dichloromethane and wash with saturated aqueous NaHCO3. Dry the organic phase over Na2SO4, filter and concentrate in vacuo to provide the title compound as oil (115 mg, 100%). GC-MS m/z: 291 (M4).

Workup

  1. temperatureAllow the mixture to warm to room temperature
  2. washwash with saturated aqueous NaHCO3
  3. dry with materialDry the organic phase over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-3f72b3bfdb584e839559dfa270ae8a7f
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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