Water → HCID 86585682, compound

HRID 2099346Notes

Reaction equation

HRID 2099346 reaction equation
COCCN(S(F)(F)[F:11])CCOC.ClC1C=CC(C(C(OCC)=O)(C2[CH:29]=[CH:28][C:26]([Cl:27])=[CH:25]C=2)O)=CC=1.[Cl:35][C:36]1[CH:41]=CC(C(C(OCC)=O)(C2C=CC(Cl)=CC=2)O)=CC=1.[C@@:56]12([OH:65])[N:63]([CH3:64])[C@@H:60]([CH2:61][CH2:62]1)[CH2:59][CH:58]=[CH:57]2.O.[C:67]([O-:70])(O)=[O:68].[Na+]>ClCCl>[C@@:56]12([OH:65])[N:63]([CH3:64])[C@@H:60]([CH2:61][CH2:62]1)[CH2:59][CH:58]=[CH:57]2.[F:11][C:59]([C:58]1[CH:57]=[CH:29][CH:28]=[C:26]([Cl:27])[CH:25]=1)([C:60]1[CH:61]=[CH:62][CH:56]=[C:36]([Cl:35])[CH:41]=1)[C:67]([O-:70])=[O:68]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 131727549HCID 131727549, compound

Product 1

HCID 86585682HCID 86585682, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.48 g (0.0067 mol) of bis-(2-methoxyethyl)aminosulfur trifluoride is used in 10 mL of dichloromethane and within 20 minutes at 15° C.-20° C., a solution of 2.09 g of 5g in 65 mL of dichloromethane is added dropwise. The mixture is stirred for 20 hours at ambient temperature, cooled to 0° C., and carefully combined 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 again extracted 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: 1.20 g of white crystals (53% of theory); melting point: 136° C.-137° C.

Workup

  1. temperaturecooled to 0° C.
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is again extracted 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-9a2bbfc594ca4f7a9ed3f2e657c913c4
Source dataset
uspto-grants-2009_08
Patent number
US07569581B2

Reaction notes

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