Acetic Acid → HCID 178423563, compound

HRID 1810478Notes

Reaction equation

HRID 1810478 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1N.[OH-].[K+].[C:12](=[S:14])=S.C(O)(=[O:17])C>O.CO>[CH3:9][C:4]1[CH:5]=[CH:6][C:7]2[O:17][C:12]([SH:14])=[N:1][C:2]=2[CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6348Carbon DisulfideHCID 103323,4-DiaminotolueneHCID 14797Potassium Hydroxide

Product 1

HCID 178423563HCID 178423563, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of 3,4-diaminotoluene (20.0 g, 162.6 mmol) and potassium hydroxide (11.36 g, 203.0 mmol) in H2O (40 mL) and MeOH (150 mL) was added carbon disulfide (13.3 mL, 220.8 mmol) slowly via syringe, and the reaction was heated to 78° C. for 2.5 hours. The mixture was poured over a mixture of ice (200 mL) and acetic acid (30 mL), and thick yellow precipitate formed. The mixture was stirred at 45° C. for 30 minutes, and then filtered to collect the solid precipitate, which was washed twice with H2O (40 mL total). The filter cake was triturated in a minimum of EtOAc, and then filtered and dried to give the title compound.

Workup

  1. customformed
  2. filtrationfiltered
  3. customto collect the solid precipitate, which
  4. washwas washed twice with H2O (40 mL total)
  5. customThe filter cake was triturated in a minimum of EtOAc
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-e4696c98aaf849e1ba9ca5c09d3e94fd
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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