Methylhydrazine → HCID 67214036, compound

HRID 2092904Notes

Reaction equation

HRID 2092904 reaction equation
[Cl-].[CH3:2][C:3]1[SH+:4][CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1.[CH3:12][NH:13]N.C(O[C:19](=[O:21])[CH3:20])(=O)C.[CH:22]([N:25]([CH2:29]C)C(C)C)([CH3:24])[CH3:23].C(#[N:33])C>O>[CH3:12][NH:13][C:10]1[CH:9]=[CH:8][C:2]2[N:33]([C:19](=[O:21])[CH3:20])[C:6]3[C:5]([S:4][C:3]=2[CH:11]=1)=[CH:24][C:22]([NH:25][CH3:29])=[CH:23][CH:7]=3

Participants

7

Reactant 5

HCID 6061MethylhydrazineHCID 6342AcetonitrileHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 86628030HCID 86628030, compound

Product 1

HCID 67214036HCID 67214036, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

To a 1000 cm3 round bottom flask placed under an atmosphere of argon was added methylthioninium chloride (Medex™) (MTC.3H2O, MW 373.90, 50 g, 134 mmol) and acetonitrile (250 cm3). Methylhydrazine (MeNHNH2, MW 46.07, 14.26 cm3, 268 mmol) was added in portions. The mixture was heated to 35° C. and stirred for 20 minutes. The resulting brown suspension was cooled to 5° C. using an ice-water bath. Acetic anhydride ((H3CCO)2O, MW 102.09, 101 cm3, 1.0 mol) and N,N-diisopropylethylamine (MW 129.24, 46.7 cm3, 268 mmol) were added, and the resulting solution was heated at 100° C. for 2 hours with stirring. The reaction mixture was cooled to 5° C. and then had water (250 cm3) added while stirring to give a light green solid, which was filtered using a standard Buchner funnel apparatus with a water aspirator, washed with water (4×30 cm3), and dried in an oven at 60° C. for 3 hours to yield the title compound, which was purified from hot ethanol (120 cm3) by cooling the solution to 5° C. using an ice-water bath so that a precipitate formed and filtering using a standard Buchner filter with a water aspirator in order to collect the crystals. The crystals were then dried in an oven at 60° C. for 3 hours (MW 327.45, 30.71 g, 93.8 mmol, yield 70%).

Workup

  1. customTo a 1000 cm3 round bottom flask placed under an atmosphere of argon
  2. temperatureThe resulting brown suspension was cooled to 5° C.
  3. temperaturethe resulting solution was heated at 100° C. for 2 hours
  4. stirringwith stirring
  5. temperatureThe reaction mixture was cooled to 5° C.
  6. additionadded
  7. stirringwhile stirring
  8. customto give a light green solid, which
  9. filtrationwas filtered
  10. washwashed with water (4×30 cm3)
  11. customdried in an oven at 60° C. for 3 hours

Sources & evidence

ORD record
ord-fcdb8737c73640dcbd0661e1da5c2fe7
Source dataset
uspto-grants-2013_05
Patent number
US08440821B2

Reaction notes

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