Ammonia → 3-(3-Benzothiazol-6-yl-2-oxo-imidazolidin-1-yl)-isonicotinamide

HRID 80248Notes

Reaction equation

HRID 80248 reaction equation
C(O[C:4](=[O:26])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[N:11]1[CH2:15][CH2:14][N:13]([C:16]2[CH:24]=[CH:23][C:19]3[N:20]=[CH:21][S:22][C:18]=3[CH:17]=2)[C:12]1=[O:25])C.CO.[NH3:29]>C(Cl)(Cl)Cl>[S:22]1[C:18]2[CH:17]=[C:16]([N:13]3[CH2:14][CH2:15][N:11]([C:6]4[CH:7]=[N:8][CH:9]=[CH:10][C:5]=4[C:4]([NH2:29])=[O:26])[C:12]3=[O:25])[CH:24]=[CH:23][C:19]=2[N:20]=[CH:21]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 59636151HCID 59636151, compound

Product 1

HCID 498727453-(3-Benzothiazol-6-yl-2-oxo-imidazolidin-1-yl)-isonicotinamideYield 28.57%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

3-(3-Benzothiazol-6-yl-2-oxo-imidazolidin-1-yl)-isonicotinic acid ethyl ester (I-185a: 0.16 g, 0.4 mmol) in methanolic ammonia (20 mL) was taken in a reaction flask and the flask was heated to 40° C. overnight. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was cooled to room temperature and concentrated. The concentrate was partitioned between DCM and water. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (10% MeOH in CHCl3) afforded 40 mg of the product (28.57% yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe concentrate was partitioned between DCM and water
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (10% MeOH in CHCl3)

Sources & evidence

ORD record
ord-ea83181ef1864b33ba3e57c6fde33134
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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