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

HRID 1196479Notes

Reaction equation

HRID 1196479 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 filtered off 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 the residue
  5. stirring200 ml of ether, whereupon the mixture is stirred for about 30 minutes
  6. filtrationThe separated crystals are filtered off 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 the red-violet crystals
  11. washare washed with water
  12. customdried in vacuo

Sources & evidence

ORD record
ord-958eb4cec04446c1a242b00a5799ebce
Source dataset
uspto-grants-1992_05
Patent number
US05114934

Reaction notes

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