Ethyl Acetate → 1-Benzothiazol-6-yl-imidazolidin-2-one

HRID 80110Notes

Reaction equation

HRID 80110 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]([NH:13][CH2:14][CH2:15]Cl)=[O:12])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[H-].[Na+].C(OCC)(=O)C>CN(C=O)C.C1COCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:15][CH2:14][NH:13][C:11]3=[O:12])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 687839281-Benzothiazol-6-yl-3-(2-chloro-ethyl)-urea

Product 1

HCID 666785541-Benzothiazol-6-yl-imidazolidin-2-oneYield 99.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Benzothiazol-6-yl-3-(2-chloro-ethyl)-urea (I-84a: 2.7 g, 10.58 mmol) in dry DMF (80 mL) was added dropwise to a stirred mixture of sodium hydride (0.76 g, 31.74 mmol) in THF (100 mL) over a period of 20 minutes at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC (100% ethyl acetate). The reaction mixture was quenched with MeOH (6 mL), concentrated under reduced pressure, followed by the addition of ice. The precipitate was collected and dried under reduced pressure to afford 2.3 g (85.18% yield) of 1-benzothiazol-6-yl-imidazolidin-2-one as the required product.

Workup

  1. customThe reaction mixture was quenched with MeOH (6 mL)
  2. concentrationconcentrated under reduced pressure
  3. additionfollowed by the addition of ice
  4. customThe precipitate was collected
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-031f203d5d2044968f183f34bc50634c
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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