(5-Nitro-2-phenyl-benzothiazole-4-yl)-acetonitrile → 2-Phenyl-6,8-dihydro-thiazolo[4,5-e]indol-7-one

HRID 1531144Notes

Reaction equation

HRID 1531144 reaction equation
[N+]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:9][C:8]=2[C:18]=1[CH2:19][C:20]#[N:21])([O-])=O.[OH:22]S(O)(=O)=O.O>O.C(O)(=O)C.[Zn]>[C:12]1([C:10]2[S:11][C:7]3[C:8]([N:9]=2)=[C:18]2[C:4](=[CH:5][CH:6]=3)[NH:21][C:20](=[O:22])[CH2:19]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 21253423(5-Nitro-2-phenyl-benzothiazole-4-yl)-acetonitrile2×HCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 212534252-Phenyl-6,8-dihydro-thiazolo[4,5-e]indol-7-one

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (5-nitro-2-phenyl-benzothiazole-4-yl)-acetonitrile (204.2 mg 0.692 mmol) (Starting Material 6) was suspended in concentrated H2SO4/H2O (1/1, 3 mL)) and stirred at 100° C. for 30 min. The resulting solution was diluted with water and extracted with ethyl acetate, and the combined organic extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to give the crude acid. To a solution of the crude acid in acetic acid (5 mL) heated at reflux was added excess zinc dust (0.45 g, 6.92 mmol) portionwise during thirty minutes. The mixture was filtered through a Celite® pad and washed with hot DMF. The solvent was removed in vacuo and residue was suspended and stirred for 30 minutes in 3M hydrochloric acid. The insoluble solid material was collected, washed with water, and air dried to give 2-phenyl-6,8-dihydro-thiazolo[4,5-e]indol-7-one. (Yield 20 mg, 11%)

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined organic extracts were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give the crude acid
  5. temperatureat reflux
  6. filtrationThe mixture was filtered through a Celite® pad
  7. washwashed with hot DMF
  8. customThe solvent was removed in vacuo and residue
  9. stirringstirred for 30 minutes in 3M hydrochloric acid
  10. customThe insoluble solid material was collected
  11. washwashed with water, and air
  12. customdried

Sources & evidence

ORD record
ord-abc802f833384de1bad9b616491641e1
Source dataset
uspto-grants-2001_03
Patent number
US06197804B1

Reaction notes

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