2-Mercaptoethanol → HCID 178428350, compound

HRID 1614305Notes

Reaction equation

HRID 1614305 reaction equation
[CH3:1][C:2]1([CH3:14])[NH:7][C:6]2[C:8]([N:10]=[C:11]([NH2:13])[NH:12][C:5]=2[NH:4][CH2:3]1)=[O:9].BrBr.SCCO>CO>[CH3:1][C:2]1([CH3:14])[CH2:3][NH:4][C:5]2[C:6]([C:8](=[O:9])[N:10]=[C:11]([NH2:13])[N:12]=2)=[N:7]1

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 24408Bromine2×HCID 1784283612-amino-6,6-dimethyl-1,5,7,8-tetrahydropteridin-4-one3×

Product 1

HCID 178428350HCID 178428350, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Quinoid-6,6-Me2PH2 is an intermediate in the synthesis of 6,6-Me2PH4 (see above). It can also be prepared quantitatively by bromine oxidation of 6,6-Me2PH4. The properties of q-6,6-Me2PH2 were determined on material made by the latter route. 6,6-Me2PH4 dihydrochloride, 0.1 mmoles, was dissolved in 3 ml methanol, and 22 mg Br2 (0.14 mmoles) was added. Removal of solvent by rotary evaporation left a dark orange film. The sample was repeatedly redissolved in 3 ml fresh methanol and evaporated to dryness for a total of 6 times, until the film was light yellow and no odor of bromine could be detected. Failure to remove the excess bromine resulted in complex absorbance changes that hindered spectral studies of q-6,6-Me2PH2. The quantitative yield was established by reduction back to 6,6-Me2PH4 using 2-mercaptoethanol, which resulting in full recovery of the original material.

Workup

  1. customRemoval of solvent
  2. customby rotary evaporation
  3. waitleft a dark orange film
  4. dissolutionThe sample was repeatedly redissolved in 3 ml fresh methanol
  5. customevaporated to dryness for a total of 6 times, until the film
  6. customFailure to remove the excess bromine
  7. customresulted in complex absorbance changes that
  8. customresulting in full recovery of the original material

Sources & evidence

ORD record
ord-79aa3588245048b7a79fe3543a4f28fe
Source dataset
uspto-grants-1993_03
Patent number
US05196533

Reaction notes

Loading…