Potassium Carbonate → HCID 21465302, compound

HRID 1940018Notes

Reaction equation

HRID 1940018 reaction equation
[NH2:1][C:2]1[C:3]([C:11]#[N:12])=[N:4][C:5]([CH2:9]Cl)=[C:6]([Cl:8])[N:7]=1.Cl.[CH3:14][NH:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[NH2:1][C:2]1[C:3]([C:11]#[N:12])=[N:4][C:5]([CH2:9][N:15]([C:16]2[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=2)[CH3:14])=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14213641HCID 14213641, compoundHCID 21465293HCID 21465293, compound

Product 1

HCID 21465302HCID 21465302, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 4 (4.04 g, 0.02 mole) and ethyl 4-methylaminobenzoate hydrochloride (3) (4.10 g, 0.02 mole) were dissolved in 200 ml of tetrahydrofuran. The solution was chilled in an ice bath, and to the solution was added slowly a potassium carbonate solution (3.0 g, 0.022 mole in 200 ml water) with stirring. After 24 hours of continuous stirring at room temperature, a yellow precipitate was collected and washed with water. Recrystallization of the product from methanol gave 2.4 g (70% yield) of yellow solid 5. This solid had a melting point of 206°-207° C. The IR spectrum (KBr) showed absorptions corresponding to --NH2 at 3389.9, 3194, and 3264 cm-1, --C≡N at 2240 cm-1, and --C(=O)O-- at 1713 cm-1. The nmr spectrum (DMSO-d6) revealed signals at 7.75 δ (2H,b,NH2), 7.70 δ (2H,d,arom), 6.67 δ (2H,d,arom), 4.35 δ (2H, s,CH2N--), 4.21 δ (2H,q,OCH2CH3), 3.20 δ (3H,s,NCH3), and 1.32 δ (3H,t,CH2CH3). The FAB mass spectrum showed a molecular ion peak at m/z 345. This peak confirmed that the molecular weight of this compound was 345. Elemental analysis confirmed the presence of C, H, N and Cl in the compound.

Workup

  1. temperatureThe solution was chilled in an ice bath
  2. stirringAfter 24 hours of continuous stirring at room temperature
  3. customa yellow precipitate was collected
  4. washwashed with water
  5. customRecrystallization of the product from methanol

Sources & evidence

ORD record
ord-5748726eeb204789bc1036d76618a77b
Source dataset
uspto-grants-1997_12
Patent number
US05698556

Reaction notes

Loading…