1-Bromo-3-chloropropane → HCID 18940733, compound

HRID 355827Notes

Reaction equation

HRID 355827 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[N:8]=[CH:9][C:10]3[NH:11][C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[N:3]=1.[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][Cl:26]>CN(C=O)C>[Cl:26][CH2:25][CH2:24][CH2:23][N:11]1[C:10]2[CH:9]=[N:8][C:7]([C:4]3[N:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 18940721HCID 18940721, compound

Product 1

HCID 18940733HCID 18940733, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-(5-methyl-1,2,4-oxadiazol-3-yl)-β-carboline (0.25 g, 0.001 mol) in anhydrous DMF (30 mL) was added 50% sodium hydride in mineral oil (0.03 g, 0.0011 mol). The mixture was stirred for 1 h at room temperature, and then carefully added to a solution of 1-bromo-3-chloropropane (0.17 g, 0.0011 mol) in anhydrous DMF (20 mL). The resulting mixture was stirred at ambient temperature for 96 h. The reaction mixture was concentrated in vacuo, and the crude product was purified twice on a silica gel column 1) (Eluent: CH2Cl2 /methanol (9:1)); 2) (Eluent: ethyl acetate/toluene (1:1)) to give the title compound 0.21 g (64%). M.p. 130°-135° C.

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature for 96 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe crude product was purified twice on a silica gel column 1) (Eluent: CH2Cl2 /methanol (9:1))

Sources & evidence

ORD record
ord-1fca670ce04c424da0bb079a5a0be0f3
Source dataset
uspto-grants-1998_11
Patent number
US05834482

Reaction notes

Loading…