Triethylamine → HCID 74020541, compound

HRID 1268965Notes

Reaction equation

HRID 1268965 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26](=[N:28][O:29][CH2:30][CH2:31][OH:32])[CH3:27])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1>ClCCl>[CH3:8][S:9]([O:32][CH2:31][CH2:30][O:29][N:28]=[C:26]([C:23]1[CH:24]=[CH:25][C:20]([C:17]2[CH:16]=[CH:15][C:14]([F:13])=[CH:19][CH:18]=2)=[CH:21][CH:22]=1)[CH3:27])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54189168HCID 54189168, compound

Product 1

HCID 74020541HCID 74020541, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.83 ml) was added dropwise at 0° C. to a solution of methanesulfonyl chloride (1.15 ml) and 2-[[1-(4′-fluoro-4-biphenylyl)ethylidene]aminoxy]ethanol (3.70 g) obtained from Reference example 26(a) in dichloromethane (40 ml), and the reaction mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were filtered off and washed with hexane and isopropyl ether to afford the target compound (4.70 g) as colorless crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe obtained crystals were filtered off
  7. washwashed with hexane and isopropyl ether

Sources & evidence

ORD record
ord-75a3aa713b9242d7885272c3030fb343
Source dataset
uspto-grants-2007_04
Patent number
US07199139B2

Reaction notes

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