Sodium Hydroxide → HCID 23449138, compound

HRID 989870Notes

Reaction equation

HRID 989870 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]2[CH:10]=[CH:9][S:8][C:7]=12.[OH-].[Na+].[C:13](Cl)(=[O:25])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1>C1COCC1.O>[N+:22]([C:19]1[CH:18]=[CH:17][C:16]([CH2:15][O:14][C:13]([NH:1][CH2:2][C:3]2[N:4]=[CH:5][N:6]3[CH:10]=[CH:9][S:8][C:7]=23)=[O:25])=[CH:21][CH:20]=1)([O-:24])=[O:23]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 782054-Nitrobenzyl chloroformateHCID 23449290HCID 23449290, compound

Product 1

HCID 23449138HCID 23449138, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-Aminomethylimidazo[5,1-b]thiazole (1.53 g) was dissolved in 50 ml of THF and 30 ml of water. A 1 N aqueous sodium hydroxide solution (12 ml) and 2.59 g of 4-nitrobenzyl chlorocarbonate were added under ice cooling to the solution. The mixture was allowed to react at the same temperature for 30 min. The reaction solution was extracted with 200 ml of ethyl acetate, followed by washing with 15% brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under the reduced pressure to about 20 ml. The resultant crystal was collected by filtration, washed with 20 ml of ethyl acetate, and dried under the reduced pressure to give 2.26 g of 7-(4-nitrobenzyloxycarbonylamino)methylimidazo-[5,1-b]thiazole.

Workup

  1. customto react at the same temperature for 30 min
  2. extractionThe reaction solution was extracted with 200 ml of ethyl acetate
  3. washby washing with 15% brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under the reduced pressure to about 20 ml
  6. filtrationThe resultant crystal was collected by filtration
  7. washwashed with 20 ml of ethyl acetate
  8. customdried under the reduced pressure

Sources & evidence

ORD record
ord-be1bffaf54cb4a7580afde77ff5e3d49
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

Loading…