Triethylamine → 3-Hydroxy-2-phenylthiazolo[3,2-b]thieno[2,3-d]pyridazin-4-ium hydroxide

HRID 1090712Notes

Reaction equation

HRID 1090712 reaction equation
[S:1]1[C:5]2[C:6](=[S:10])[NH:7][N:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.Br[CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13](Cl)=[O:14].C(N(CC)CC)C>C(Cl)Cl>[OH-:14].[OH:14][C:13]1[N+:7]2=[N:8][CH:9]=[C:4]3[CH:3]=[CH:2][S:1][C:5]3=[C:6]2[S:10][C:12]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 598182Bromophenylacetyl chlorideHCID 19913670Thieno[2,3-d]pyridazine-7(6H)-thione

Product 1

HCID 198985853-Hydroxy-2-phenylthiazolo[3,2-b]thieno[2,3-d]pyridazin-4-ium hydroxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

66.95 g of thieno[2,3-d]pyridazine-7(6H)-thione are suspended in 3200 ml of methylene chloride under argon, whereupon 102.7 g of α-bromophenylacetyl chloride are added dropwise thereto. The mixture is stirred at room temperature for about 30 minutes and then 121 ml of triethylamine are added dropwise thereto, whereby the mixture is cooled to 25°-30°. It is stirred for about 40 minutes. After evaporation of the solvent in vacuo, the residue is taken up in 1000 ml of water and 200 ml of ether, whereupon the mixture is stirred for about 30 minutes. The separated crystals are removed by filtration under suction, washed with water and ether and dried overnight. The dried crystals are again triturated with 1000 ml of water. After suction filtration, the red-violet crystals are washed with water and dried in vacuo. There is obtained 3-hydroxy-2-phenylthiazolo[3,2-b]thieno [2,3-d]-pyridazin-4-ium hydroxide (internal salt) of m.p. 260°-264° (decomposition).

Workup

  1. additionare added dropwise
  2. temperaturewhereby the mixture is cooled to 25°-30°
  3. stirringIt is stirred for about 40 minutes
  4. customAfter evaporation of the solvent in vacuo
  5. stirring200 ml of ether, whereupon the mixture is stirred for about 30 minutes
  6. customThe separated crystals are removed by filtration under suction
  7. washwashed with water and ether
  8. customdried overnight
  9. customThe dried crystals are again triturated with 1000 ml of water
  10. filtrationAfter suction filtration
  11. washthe red-violet crystals are washed with water
  12. customdried in vacuo

Sources & evidence

ORD record
ord-c6a5bc36cb8d46e292dbdcdd3be565d5
Source dataset
uspto-grants-1992_01
Patent number
US05082842

Reaction notes

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