Triethylamine → HCID 22291385, compound

HRID 967830Notes

Reaction equation

HRID 967830 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:21]([F:24])([F:23])[F:22])[N:10]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][OH:20])=[CH:14][CH:13]=3)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[CH3:32][S:33]([O:20][CH2:19][CH2:18][C:15]1[CH:16]=[CH:17][C:12]([N:10]2[CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[C:9]2[C:21]([F:23])([F:24])[F:22])=[CH:13][CH:14]=1)(=[O:35])=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22291415HCID 22291415, compound

Product 1

HCID 22291385HCID 22291385, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-{4-[4-phenyl-2-(trifluoromethyl)-1H-imidazol-1-yl]phenyl}ethanol (450 mg, 1.35 mmol) and triethylamine (377 μL, 2.70 mmol) in dichloromethane (13 mL) was added methanesulfonyl chloride (126 μL, 1.62 mmol) at ambient temperature. After 1 h, the reaction mixture was partitioned between dichloromethane and water. The aqueous phase was extracted with dichloromethane (3×10 mL) and the combined organic phase was dried (MgSO4) and concentrated under reduced pressure to give the title compound as a brown oil (quant.). MS (EI) m/z 410 [M]+.

Workup

  1. customthe reaction mixture was partitioned between dichloromethane and water
  2. extractionThe aqueous phase was extracted with dichloromethane (3×10 mL)
  3. dry with materialthe combined organic phase was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19b3581e696d4a25b9dbce0d2bdb74b9
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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