Acetonitrile → HCID 67214036, compound

HRID 2092903Notes

Reaction equation

HRID 2092903 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.O.[NH2:13]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:31](#[N:33])C>O>[CH3:31][NH:33][C:10]1[CH:9]=[CH:8][C:2]2[N:13]([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 6342AcetonitrileHCID 7918Acetic AnhydrideHCID 24654Hydrazine hydrate (1:1)HCID 81531DiisopropylethylamineHCID 86628030HCID 86628030, compound

Product 1

HCID 67214036HCID 67214036, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a 250 cm3 round bottom flask placed under an atmosphere of argon was added methylthioninium chloride (Medex™) (MTC.3H2O, MW 373.90, 10 g, 26.7 mmol) and acetonitrile (50 cm3). Hydrazine hydrate (NH2NH2.H2O, MW 50.06, 2.85 cm3, 58.7 mmol) was added in portions. The mixture was heated to 65° 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, 25 cm3, 267 mmol) and N,N-diisopropylethylamine (MW 129.24, 9.3 cm3, 53.6 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 had water (50 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 (4×6 cm3), and dried in an oven at 60° C. for 3 hours to yield the title compound, which was purified from hot ethanol (27 cm3), 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 where then dried in an oven at 60° C. for 3 hours (MW 327.45, 5.68 g, 17.4 mmol, yield 65%).

Workup

  1. customTo a 250 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 (4×6 cm3)
  11. customdried in an oven at 60° C. for 3 hours

Sources & evidence

ORD record
ord-002b659dc85d46138f57f53fa1f173c0
Source dataset
uspto-grants-2013_05
Patent number
US08440821B2

Reaction notes

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