Hydrogen Bromide → 6-Bromo-6-isothiocyanatoquinoxaline

HRID 1010576Notes

Reaction equation

HRID 1010576 reaction equation
[BrH:1].C(Cl)(Cl)=S.Br[C:7]1[C:16]([N:17]=[C:18]=[S:19])=[CH:15][CH:14]=[C:13]2[C:8]=1[N:9]=[CH:10][CH:11]=[N:12]2>O>[Br:1][C:16]1([N:17]=[C:18]=[S:19])[CH:15]=[CH:14][C:13]2[N:12]=[CH:11][CH:10]=[N:9][C:8]=2[CH2:7]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 10040ThiophosgeneHCID 44602745-Bromo-6-isothiocyanatoquinoxaline

Product 1

HCID 865956566-Bromo-6-isothiocyanatoquinoxalineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The crude hydrobromide product described above (4.27 g, 14.0 mmol) was dissolved in 60 ml of water; thiophosgene (Aldrich, 1.28 ml, 16.8 mmol) was added in small portions with vigorous stirring. After 2 hours, the red color of the solution was discharged. The solid formed was filtered off and washed thoroughly with water. After drying in vacuo at 25° C., 3.38 g of brick red crystals were obtained, m.p. 157-8° C., representing a yield of 90%. A portion of this material was further purified by column chromatography to give white crystals, m.p. 157-8° C. Using various analytical procedures, these crystals were determined to be 5-bromo-6-isothiocyanatoquinoxaline.

Workup

  1. customThe solid formed
  2. filtrationwas filtered off
  3. washwashed thoroughly with water
  4. customAfter drying in vacuo at 25° C.
  5. custom3.38 g of brick red crystals were obtained
  6. customA portion of this material was further purified by column chromatography
  7. customto give white crystals, m.p. 157-8° C

Sources & evidence

ORD record
ord-ae9087daceae42a2947dde6075641b5c
Source dataset
uspto-grants-2011_07
Patent number
US07977335B2

Reaction notes

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