Calcium Chloride → HCID 827053, compound

HRID 1739604Notes

Reaction equation

HRID 1739604 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]2[S:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH2:12][C:6]=2[CH:5]=1)([O-])=O.[Cl-].[Cl-].[Ca+2]>C(O)C.O.[Zn]>[NH2:1][C:4]1[CH:19]=[CH:18][C:7]2[S:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH2:12][C:6]=2[CH:5]=1

Participants

6

Reactant 2

HCID 5284359Calcium ChlorideHCID 12362917HCID 12362917, compound

Product 1

HCID 827053HCID 827053, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-nitro-10-oxo-dibenzo[b,f]thiepine (2.40 g, 9.30 mmol) (Coll. Czech. Chem. Commun. 1977, 42:2231) in 78% ethanol, was added a solution of CaCl2 (0.66 g, 5.90 mmol) in water (1.00 mL) followed by zinc dust (19.9 g, 30.4 mmol). The reaction mixture was refluxed for 2 h, filtered through celite and washed extensively with hot ethanol. The ethanol filtrate was concentrated to 5.00 mL and water was added to precipitate out the product. The product was filtered and dried under vacuum, purification was performed by recrystallization from EtOAc and hexane, yield 1.97 g (92.3%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. filtrationfiltered through celite
  3. washwashed extensively with hot ethanol
  4. concentrationThe ethanol filtrate was concentrated to 5.00 mL and water
  5. additionwas added
  6. customto precipitate out the product
  7. filtrationThe product was filtered
  8. customdried under vacuum, purification
  9. customwas performed by recrystallization from EtOAc and hexane, yield 1.97 g (92.3%)

Sources & evidence

ORD record
ord-0cd1a69846524e4b8648f7e7712151f5
Source dataset
uspto-grants-1999_10
Patent number
US05968478

Reaction notes

Loading…