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

HRID 2383964Notes

Reaction equation

HRID 2383964 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-aa986820b8bf43229bfde4e3068ff46d
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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