Hydrazine hydrate (1:1) → HCID 58873111, compound

HRID 1990113Notes

Reaction equation

HRID 1990113 reaction equation
C[N:2]([CH:4]=[N:5][C:6]([C:8]1[S:9][C:10]([CH2:25][CH3:26])=[C:11]([C:23]#[N:24])[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)=O)C.O.[NH2:28]N>C(O)(=O)C>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:12]2[C:11]([C:23]#[N:24])=[C:10]([CH2:25][CH3:26])[S:9][C:8]=2[C:6]2[NH:28][N:2]=[CH:4][N:5]=2)=[CH:14][CH:15]=1)([CH3:20])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58873079HCID 58873079, compound

Product 1

HCID 58873111HCID 58873111, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

Dissolve 3-(4-tert-butyl-phenyl)-4-cyano-5-ethyl-thiophene-2-carboxylic acid dimethylaminomethyleneamide (261 mg, 0.71 mmol) in 2 mL of glacial acetic acid, add hydrazine monohydrate (50 μL, 1.03 mmol) and heat to 90° C. under nitrogen. After 90 minutes cool the reaction slightly, pour into 50 mL of ice-water and stir for twenty minutes. Filter off the resulting solid and rinse with 10 mL of water. Vacuum-dry overnight to give the title compound, 206 mg (86%). MS(ES+, m/e)=337 (M++1); HPLC=00%.

Workup

  1. temperatureAfter 90 minutes cool
  2. customthe reaction slightly
  3. filtrationFilter off the resulting solid
  4. washrinse with 10 mL of water
  5. customVacuum-dry overnight

Sources & evidence

ORD record
ord-6131cae5b1dc4d428449c27eaa41f131
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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