Methanol → 1-Benzothiazol-6-yl-4,4-dimethyl-imidazolidin-2-one

HRID 80275Notes

Reaction equation

HRID 80275 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]([NH:13][C:14]([CH3:18])([CH3:17])[CH2:15]Cl)=[O:12])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[H-].[Na+].CO>C1COCC1.C(Cl)(Cl)Cl>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:15][C:14]([CH3:18])([CH3:17])[NH:13][C:11]3=[O:12])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 687898531-Benzothiazol-6-yl-3-(2-chloro-1,1-dimethyl-ethyl)-urea

Product 1

HCID 596361661-Benzothiazol-6-yl-4,4-dimethyl-imidazolidin-2-oneYield 77.35%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1-Benzothiazol-6-yl-3-(2-chloro-1,1-dimethyl-ethyl)-urea (I-201a: 620 mg, 2.18 mmol) in dry THF (5 mL) was added dropwise to a stirred mixture of NaH (78 mg, 3.25 mmol) in dry THF (5 mL) under argon atmosphere over a period of 10 minutes at 0° C. The resulting reaction mixture was stirred at room temperature for 45 minutes. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was partitioned between chilled water and ethylacetate. The organic layer was dried over Na2SO4 and concentrated to afford 410 mg of the product (77.35% yield).

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was partitioned
  3. temperaturebetween chilled water and ethylacetate
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-46c100718ae141709dd4fdb50e7d0e3d
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

Loading…