Hydrochloric Acid → HCID 86741446, compound

HRID 543071Notes

Reaction equation

HRID 543071 reaction equation
[Cl:1][TeH:2]1(Cl)(Cl)[C:7]2[CH:8]=[CH:9][C:10]([S:12][CH3:13])=[CH:11][C:6]=2[NH+:5]=[C:4]([CH3:14])O1.[OH-].[Na+].[BH4-].[Na+].Cl>CO.O>[Cl-:1].[CH3:14][CH:4]1[NH2+:5][C:6]2[CH:11]=[C:10]([S:12][CH3:13])[CH:9]=[CH:8][C:7]=2[Te:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride3×HCID 131715115HCID 131715115, compound

Product 1

HCID 86741446HCID 86741446, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1,1,1-Trichloro-3-methyl-6-methylthio-2,1,4-benzoxatellurazinium, inner salt (Example 10) (20.7 g=0.05 mole) was placed in methanol (200 ml), and sodium hydroxide (4 g=0.1 mole) dissolved in water (10 ml) was added. The material did not completely dissolve. Sodium borohydride was added in portions with stirring under a nitrogen atmosphere. The starting material underwent vivid color changes to orange and then to blue with the addition of each portion of reducing agent. The mass became difficult to stir. Eventually, the reaction mixture became more liquid, though the orange color kept returning after each portion was added, as the rather insoluble starting material underwent the first reduction step. The reaction mixture was kept overnight under an atmosphere of nitrogen. The reduction was continued the next day by heating the mixture to near reflux temperature while sodium borohydride was being added. When the stage was reached where the reaction turned colorless after a portion was added and the orange color did not return upon further stirring (after the addition of 6.65 g=0.175 mole sodium borohydride), the mixture was cooled to ≃10° C. and concentrated hydrochloric acid (50 ml=0.5 mole) was added in one portion. The mixture turned orange, then yellow, and a copious beige precipitate formed. This was stirred for 45 minutes and then collected by filtration to yield 27.5 g solids. On recrystallization from methanol (300 ml), using Celite® to clarify the solution, there were obtained 13.5 g, 81.9% of theory, cream colored needles, m.p. 130°-145° C. (dec.).

Workup

  1. additionwas added
  2. dissolutionThe material did not completely dissolve
  3. additionThe starting material underwent vivid color changes to orange and then to blue with the addition of each portion
  4. stirringto stir
  5. additionwas added
  6. additionwas being added
  7. additionwas added
  8. stirringupon further stirring (
  9. temperaturewas cooled
  10. customto ≃10° C.
  11. customyellow, and a copious beige precipitate formed
  12. stirringThis was stirred for 45 minutes
  13. filtrationcollected by filtration

Sources & evidence

ORD record
ord-cd3898d1e3434e30b002ccc8533565a5
Source dataset
uspto-grants-1987_04
Patent number
US04661438

Reaction notes

Loading…