Hydrazine hydrate (1:1) → HCID 69443896, compound

HRID 1028463Notes

Reaction equation

HRID 1028463 reaction equation
[CH:1]([O:4][C:5]1[CH:35]=[CH:34][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]([N:23]4C(=O)C5C(=CC=CC=5)C4=O)[CH3:22])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].O.NN>C(Cl)Cl.C(O)C>[CH:1]([O:4][C:5]1[CH:35]=[CH:34][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]([NH2:23])[CH3:22])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69443135HCID 69443135, compound

Product 1

HCID 69443896HCID 69443896, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 1E (0.65 g, 0.0013 mol) in a mixture of methylene chloride (20 mL) and ethanol (2 mL) was added hydrazine monohydrate (0.66 g, 0.013 mol) and the mixture was refluxed under nitrogen for 2 hours. The white suspension was cooled to room temperature, concentrated, dissolved in methylene chloride, and filtered. The filtrate was concentrated to give 0.46 g of the title compound, which was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 1.35 (d, J=5.88 Hz, 6 H) 139 (d, J=6.62 Hz, 3 H) 4.13 (q, J=6.62 Hz, 1 H) 4.44-4.62 (m, 1 H) 6.86-6.98 (m, 2 H) 7.16-7.25 (m, 2 H) 7.30-7.44 (m, 5 H). MS (ESI), m/z 337.7 (M−17)+.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 2 hours
  2. concentrationconcentrated
  3. dissolutiondissolved in methylene chloride
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-add3f119621e49e1bd9de80a4e61256e
Source dataset
uspto-grants-2014_05
Patent number
US08735595B2

Reaction notes

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