Hydrochloric Acid → Biuret, 1-phenyl-2,4-dithio-

HRID 968881Notes

Reaction equation

HRID 968881 reaction equation
[OH-].[Na+].[NH2:3][C:4]([NH2:6])=[S:5].[C:7]1([N:13]=[C:14]=[S:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl>O.CC#N>[C:7]1([NH:13][C:14]([NH:3][C:4]([NH2:6])=[S:5])=[S:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7673Phenyl IsothiocyanateHCID 14798Sodium HydroxideHCID 2723790Thiourea

Product 1

HCID 3032513Biuret, 1-phenyl-2,4-dithio-Yield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a stirring solution of NaOH (0.52 g, 13.1 mmol) in 60 mL of 10% H2O:CH3CN was added thiourea (1.0 g, 13.1 mmol). The resulting suspension was heated to 40° C. for 20 min. and then cooled to RT. To this mixture was added phenylisothiocyanate (1.5 ml, 13.1 mmol), and the clear yellow solution was stirred overnight. After stirring for 12 h, 1 N HCl was added until a white precipitate formed. The precipitate was filtered, washed with H2O, and dried under vacuum to produce the title compound as a light yellow powder (0.78 g, 30%). 1H-NMR (400 MHz, d6-DMSO) δ7.25 (t, 2H, J=7.3 Hz), 7.40 (t, 2H, J=7.9 Hz), 7.56 (d, 1H, J=7.9 Hz), 9.13-9.29 (broad singlet, 1H), and 10.26-10.79 (broad singlet, 2H).

Workup

  1. temperaturecooled to RT
  2. stirringAfter stirring for 12 h
  3. customformed
  4. filtrationThe precipitate was filtered
  5. washwashed with H2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-348f13fa09404c4c813cd79233b41ba5
Source dataset
uspto-grants-2007_12
Patent number
US07304082B2

Reaction notes

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