Dichloromethane → HCID 22902175, compound

HRID 1489769Notes

Reaction equation

HRID 1489769 reaction equation
[CH2:1]([O:8][C:9]([NH:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20](Cl)Cl.BrN1[C:28](=O)[CH2:27][CH2:26][C:25]1=O>>[C:16]([O:15][C:13]([N:12]1[N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH:28]2[CH2:20][CH:25]1[CH:26]=[CH:27]2)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 11288582Benzyl tert-butyl hydrazine-1,2-dicarboxylate

Product 1

HCID 22902175HCID 22902175, compoundYield 54%

Procedure

To a stirred mixture of 1 g (4.34 mmol) of 1-benzyloxycarbonyl-2-t-butoxycarbonylhydrazine (Dutta et al., J.C.S. Perkin I, 1975, 1712-1720) in 30 ml of anhydrous methylene chloride 1.55 g (8.7 mmol) of N-bromosuccinimide was added at 0° C. and the stirring was continued for 1 hour with external cooling in an ice bath. The reaction mixture was washed with 10% aqueous sodium thiosulfate solution and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated to dryness in vacuo. The residue was redissolved in 15 ml of anhydrous ether, 0.57 g (8.7 mmol) of freshly distilled cyclopentadiene was added and the mixture was allowed to stay for I hour at room temperature. Evaporation to dryness under reduced pressure gave 0.77g (54% yield) of the title product as a colorless syrup; NMR (CDCl3) 1.44 (s, 9H, t-butoxy CH3); 1.7 (m, 2H, CH2 -7); 5.06 (m, 2H, CH-1,4); 5.15 (s, 2H, methoxy CH2); 6A (m, 2H, CH-5,6); 7.24 (m, 5H, aromatic).

Workup

  1. additionwas added at 0° C.
  2. temperaturewith external cooling in an ice bath
  3. washThe reaction mixture was washed with 10% aqueous sodium thiosulfate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated to dryness in vacuo
  6. dissolutionThe residue was redissolved in 15 ml of anhydrous ether
  7. addition0.57 g (8.7 mmol) of freshly distilled cyclopentadiene was added
  8. customto stay for I hour at room temperature
  9. customEvaporation to dryness under reduced pressure

Sources & evidence

ORD record
ord-e001068222a446be9384e87d6ac97713
Source dataset
uspto-grants-1997_10
Patent number
US05679688

Reaction notes

Loading…