Water → HCID 86585676, compound

HRID 2099340Notes

Reaction equation

HRID 2099340 reaction equation
COCCN(S(F)(F)[F:11])CCOC.[F:14][C:15]1[CH:16]=[C:17]([CH:40]=[CH:41][C:42]=1[F:43])[C:18]([C:32]1[CH:37]=[CH:36][C:35]([F:38])=[C:34]([F:39])[CH:33]=1)(O)[C:19]([O:21][C@@:22]12[N:29]([CH3:30])[C@@H:26]([CH2:27][CH2:28]1)[CH2:25][CH:24]=[CH:23]2)=[O:20].O.C([O-])(O)=O.[Na+]>ClCCl>[C@@:22]12([OH:21])[N:29]([CH3:30])[C@@H:26]([CH2:27][CH2:28]1)[CH2:25][CH:24]=[CH:23]2.[F:11][C:18]([C:32]1[CH:37]=[CH:36][C:35]([F:38])=[C:34]([F:39])[CH:33]=1)([C:17]1[CH:40]=[CH:41][C:42]([F:43])=[C:15]([F:14])[CH:16]=1)[C:19]([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 86585675HCID 86585675, compound

Product 1

HCID 86585676HCID 86585676, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.66 g (0.012 mol) of bis-(2-methoxyethyl)aminosulfur trifluoride were placed in 10 mL of dichloromethane and within 20 minutes a solution of 0.01 mol of 5b in 65 mL of dichloromethane was added dropwise at 15° C.-20° C. The mixture is stirred for 20 hours at ambient temperature, cooled to 0° C. and carefully mixed with 80 mL of water with thorough stirring. The mixture is then carefully adjusted to pH 8 with aqueous NaHCO3 solution, the organic phase is separated off, the aqueous phase is extracted again with dichloromethane, the combined organic phases are washed with water, dried over MgSO4, and evaporated to dryness. The hydrochloride is precipitated and recrystallized from acetonitrile/diethylether. Yield: 2.60 g of white crystals (57% of theory); melting point: 233° C.

Workup

  1. temperaturecooled to 0° C.
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is extracted again with dichloromethane
  4. washthe combined organic phases are washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customThe hydrochloride is precipitated
  8. customrecrystallized from acetonitrile/diethylether

Sources & evidence

ORD record
ord-3f0b7375387242cdb8fb4eefb8314e9a
Source dataset
uspto-grants-2009_08
Patent number
US07569581B2

Reaction notes

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