Kinetin → HCID 14035908, compound

HRID 1506568

Reaction equation

HRID 1506568 reaction equation
[CH:1]1[CH:2]=[C:3]([CH2:6][NH:7][C:8]2[N:16]=[CH:15][N:14]=[C:10]3[N:11]=[CH:12][NH:13][C:9]=23)[O:4][CH:5]=1.Br[CH2:18][CH2:19][Cl:20].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH2:6]([NH:7][C:8]1[N:16]=[CH:15][N:14]=[C:10]2[C:9]=1[N:13]=[CH:12][N:11]2[CH2:18][CH2:19][Cl:20])[C:3]1[O:4][CH:5]=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 3830KinetinHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium Carbonate

Product 1

HCID 14035908HCID 14035908, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Kinetin (2 g, 9.3 mmol), 1-bromo-2-chloroethane (1.3 g, 9.1 mmol) and K2CO3 (2.5 g, 24 mmol) were mixed in 100 ml dimethylsulfoxide (DMSO) for 18 h. The reaction mixture was poured onto 200 ml drift ice and then extracted in ethyl acetate and dried over Na2SO4. The ethyl acetate layer was evaporated in vacuo. The pure product of white powder character was recrystallised from methanol. Yield: 80%. 1H NMR (DMSO-d6): 4.07 (2H, t, J=5.82), 4.52 (2H, t, J=5.82), 4.70 (2H, s (br)), 6.23 (1H, d, J=2.67), 6.35 (1H, m), 7.53 (1H, d, J=2.67), 8.22 (2H, m), 8.25 (1H, s)

Workup

  1. additionThe reaction mixture was poured onto 200 ml
  2. extractionextracted in ethyl acetate
  3. dry with materialdried over Na2SO4
  4. customThe ethyl acetate layer was evaporated in vacuo
  5. customThe pure product of white powder character was recrystallised from methanol

Sources & evidence

ORD record
ord-c18c315c182e4ba582e80e42200137a9
Source dataset
uspto-grants-2015_12
Patent number
US09220269B2

Linked notes

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