Methanol → 1-Benzothiazol-6-yl-4-ethyl-3-(4-methyl-pyridin-3-yl)-1,3-dihydro-imidazol-2-one

HRID 80222Notes

Reaction equation

HRID 80222 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]([CH2:21][C:22](=O)[CH2:23][CH3:24])[C:11]([NH:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:19]=3[CH3:20])=[O:12])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.CO>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH:21]=[C:22]([CH2:23][CH3:24])[N:13]([C:14]4[CH:15]=[N:16][CH:17]=[CH:18][C:19]=4[CH3:20])[C:11]3=[O:12])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 887MethanolHCID 59636266HCID 59636266, compound

Product 1

HCID 498725551-Benzothiazol-6-yl-4-ethyl-3-(4-methyl-pyridin-3-yl)-1,3-dihydro-imidazol-2-oneYield 28.57%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

1-Benzothiazol-6-yl-3-(4-methyl-pyridin-3-yl)-1-(2-oxo-butyl)-urea (I-168b: 185 mg, 0.522 mmol) in toluene (15 mL) was refluxed at 120° C. for 20 hours. The reaction was monitored by TLC (5% MeOH in chloroform). The reaction mixture was concentrated under reduced pressure and the crude residue was purified by column chromatography on silica gel (2.5% methanol in chloroform) to afford 50 mg of the product (28.57% yield).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude residue was purified by column chromatography on silica gel (2.5% methanol in chloroform)

Sources & evidence

ORD record
ord-d6cab1232810428fbfa42b92d00088bc
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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