Potassium Carbonate → 5,6-Dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

HRID 1013365Notes

Reaction equation

HRID 1013365 reaction equation
C([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][C:12]3[C:18]([Br:19])=[C:17]([Br:20])[S:16][C:13]=32)[CH2:9]1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].ClC(OC(Cl)C)=O>ClC(Cl)C.CO>[Br:20][C:17]1[S:16][C:13]2[CH:14]3[CH:10]([CH2:11][C:12]=2[C:18]=1[Br:19])[CH2:9][NH:8][CH2:15]3

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5213051-Chloroethyl chloroformateHCID 1317270302-Benzyl-5,6-dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

Product 1

HCID 597894515,6-Dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
22 °C

Procedure

The product from step g) (605 mg, 1.46 mmol) in dichloroethane (7 ml) was treated with powdered K2CO3 (806 mg, 5.84 mmol) and 1-chloroethyl chloroformate (Ace-Cl) (632 μl, 5.84 mmol) at 80° C. for 16 hours. Next, the reaction was cooled, filtered and concentrated providing an oily residue. This oily residue was diluted with anhydrous MeOH (15 ml) and stirred for 1 hour at 22° C. The solvent was concentrated and the crude residue was purified by preparative LC/MS providing title compound. 1H NMR (300 MHz, CD3OD, ppm) 2.65-2.75 (m, 1H); 3.05-3.30 (m, 2H); 3.32-3.80 (m, 4H); 4.10-4.28 (br m, 1H); MS calculated for C9H9Br2NS+H 324, observed 322, 324, 326.

Workup

  1. temperatureNext, the reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customproviding an oily residue
  5. concentrationThe solvent was concentrated
  6. customthe crude residue was purified by preparative LC/MS

Sources & evidence

ORD record
ord-a71c7532544e490cbe90a3d9066e4d16
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

Loading…