HCID 10686686, compound → HCID 12831508, compound

HRID 615171Notes

Reaction equation

HRID 615171 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[N:16]=O)[C:13]2[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=2[S:11]3)=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[NH2:16][C:15]1[N:14]2[C:10]([S:11][C:12]3[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=32)=[N:9][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 10686686HCID 10686686, compound

Product 1

HCID 12831508HCID 12831508, compoundYield 26.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

While suspending 9 g of 2-(p-chlorophenyl)-3-nitrosoimidazo[2,1-b]benzothiazole in 200 ml of acetic acid, 6 g of zinc powder was gradually added to the suspension at temperatures below 15° C. Insoluble materials were filtered away and 3 drops of concentrated sulfuric acid were added to the filtrate to form precipitates. After filtering away the precipitates, 20 ml of concentrated sulfuric acid was added to the mother liquor and the mixture was allowed to stand overnight. The crystals which formed were recovered by filtration and added to a mixture of ethyl acetate and water. After adding thereto potassium carbonate followed by stirring, the ethyl acetate layer which formed was recovered, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to form crystals, which were recovered and recrystallized from toluene to provide 2.3 g of 3-amino-2-(p-chlorophenyl)imidazo[2,1-b]benzothiazole.

Workup

  1. additionwas gradually added to the suspension at temperatures below 15° C
  2. filtrationInsoluble materials were filtered away
  3. addition3 drops of concentrated sulfuric acid were added to the filtrate
  4. customto form
  5. customprecipitates
  6. filtrationAfter filtering away the precipitates, 20 ml of concentrated sulfuric acid
  7. additionwas added to the mother liquor
  8. customThe crystals which formed
  9. filtrationwere recovered by filtration
  10. additionadded to a mixture of ethyl acetate and water
  11. additionAfter adding
  12. customthe ethyl acetate layer which formed
  13. customwas recovered
  14. washwashed with water
  15. dry with materialdried with anhydrous magnesium sulfate
  16. concentrationconcentrated under reduced pressure
  17. customto form crystals, which
  18. customwere recovered
  19. customrecrystallized from toluene

Sources & evidence

ORD record
ord-746f4639c6784bf7b0f8c70186477366
Source dataset
uspto-grants-1985_02
Patent number
US04497817

Reaction notes

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