Water → HCID 19075958, compound

HRID 965172Notes

Reaction equation

HRID 965172 reaction equation
NN.[C:3]([C:6]1[O:7][C:8]2[C:9](=[C:11]([S:17]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:19])=[O:18])[CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=1)(=O)[CH3:4].C(=O)([O-])[O-].[K+].[K+].O>C=C.[Cl-].[Na+].O.C(OCC)(=O)C>[CH2:21]([NH:20][S:17]([C:11]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:8]2[O:7][C:6]([CH2:3][CH3:4])=[CH:10][C:9]=12)(=[O:19])=[O:18])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 962WaterHCID 9321HydrazineHCID 11430Potassium CarbonateHCID 9928769HCID 9928769, compound

Product 1

HCID 19075958HCID 19075958, compoundYield 53.1%

Reagents, catalysts & solvents 3

HCID 6325EthyleneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Hydrazine (6.96 g) was added to a suspension of Example 2 (10 g) in ethylene glygol (120 ml) at 38° C. The mixture was heated and potassium carbonate (7.7 g) was added at 65° C. Heating was continued until a temperature of 170° C. was attained. The mixture was cooled to room temperature and poured into a mixture of brine (300 ml), water (300 ml) and ethyl acetate (300 ml). The aqueous layer was extracted with ethyl acetate (2×300 ml) and the combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was applied to a silica column and eluted with 30% ethyl acetate in heptane to provide the title compound as an off-white solid (5.1 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureHeating
  3. customwas continued until a temperature of 170° C.
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×300 ml)
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. washeluted with 30% ethyl acetate in heptane

Sources & evidence

ORD record
ord-56a9e3bc4375480085ee2f75dfb12ad6
Source dataset
uspto-grants-1998_06
Patent number
US05773467

Reaction notes

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