Coumarin 343 → Coumarin propyl azide

HRID 217559Notes

Reaction equation

HRID 217559 reaction equation
C1CN2[C:4]3[C:5](CCC2)=[C:6]2[O:13][C:11](=[O:12])[C:10](C(O)=O)=[CH:9][C:7]2=[CH:8][C:3]=3C1.[N:22]([CH2:25][CH2:26][CH2:27]O)=[N+:23]=[N-:24].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:25]([N:22]=[N+:23]=[N-:24])[CH2:26][CH3:27].[O:13]1[C:6]2[C:7](=[CH:8][CH:3]=[CH:4][CH:5]=2)[CH:9]=[CH:10][C:11]1=[O:12]

Participants

6

Reactant 3

HCID 108770Coumarin 343HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109969743-Azidopropan-1-ol

Product 1

HCID 131729764Coumarin propyl azideYield 30%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Coumarin 343 (0.285 g, 1.00 mmol) and 3-azido-1-propanol (0.505 g, 5.00 mmol) in CH2Cl2 (20 mL) was cooled to 0° C. and EDC.HCl (0.575 g, 3.00 mmol) and DMAP (0.006 g, 0.05 mmol) were sequentially added. The orange solution was stirred at 0° C. for 2 h, then at ambient temperature overnight. The reaction mixture was washed with water (2×50 mL) and dried over MgSO4. The volatiles were removed under reduced pressure and the crude product purified by flash chromatography (CC, SiO2, 1) 100% CH2Cl2; 2) CH2Cl2/Et2O 10:1). The isolated product still contained some 3-azido-1-propanol starting material, which was then removed by coevaporation with toluene under reduced pressure. Obtained 0.110 g (0.299 mmol, 30%) of (28) as an orange oil that partially solidified by standing at ambient temperature over several days.

Workup

  1. customat ambient temperature
  2. customovernight
  3. washThe reaction mixture was washed with water (2×50 mL)
  4. dry with materialdried over MgSO4
  5. customThe volatiles were removed under reduced pressure
  6. customthe crude product purified by flash chromatography (CC, SiO2, 1) 100% CH2Cl2
  7. customwas then removed by coevaporation with toluene under reduced pressure

Sources & evidence

ORD record
ord-db71b9fee9534413819026d68d7cad4f
Source dataset
uspto-grants-2012_06
Patent number
US08197847B2

Reaction notes

Loading…