Bromine → HCID 19016794, compound

HRID 1728930Notes

Reaction equation

HRID 1728930 reaction equation
[CH2:1]([C:3]1[S:17][C:6]2[S:7][CH2:8][CH2:9][CH:10]3[CH2:15][C:14](=[O:16])[NH:13][N:12]=[C:11]3[C:5]=2[CH:4]=1)[CH3:2].BrBr>C(O)(=O)C>[CH2:1]([C:3]1[S:17][C:6]2[S:7][CH2:8][CH2:9][C:10]3[C:11](=[N:12][NH:13][C:14](=[O:16])[CH:15]=3)[C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 19016825HCID 19016825, compound

Product 1

HCID 19016794HCID 19016794, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 3.7 g of 9-ethyl-4,4a,5,6-tetrahydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one in 40 ml of acetic acid is added dropwise a solution of 2.3 g of bromine in 10 ml of acetic acid with stirring for 15 minutes at 45°-50° C. and the mixture is stirred for 30 minutes at the same temperature. Then, the mixture is poured into ice-cold water and the precipitated crystals are collected by filtration and washed with water. The resulting crude crystals are dissolved in chloroform, subjected to column chromatography on silica gel and eluted with a mixed solvent of chloroform and ethanol (100:0.5). The crystals obtained from the fraction are recrystallized from a mixed solvent of chloroform and ethanol to give 1.8 g of 9-ethyl-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one as white crystals, melting at 256°-258° C.

Workup

  1. stirringthe mixture is stirred for 30 minutes at the same temperature
  2. additionThen, the mixture is poured into ice-cold water
  3. filtrationthe precipitated crystals are collected by filtration
  4. washwashed with water
  5. dissolutionThe resulting crude crystals are dissolved in chloroform
  6. washeluted with a mixed solvent of chloroform and ethanol (100:0.5)
  7. customThe crystals obtained from the fraction
  8. customare recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-46f645c9edda4506a7e9f045068d50db
Source dataset
uspto-grants-1994_07
Patent number
US05329016

Reaction notes

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