Sodium hydride → HCID 53823975, compound

HRID 1728341Notes

Reaction equation

HRID 1728341 reaction equation
[C:1]([N:3]=[C:4]1[NH:8][CH2:7][CH2:6][S:5]1)#[N:2].[H-].[Na+].Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>CN(C)C=O>[C:1]([N:3]=[C:4]1[N:8]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH2:6][S:5]1)#[N:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 178512079HCID 178512079, compound

Product 1

HCID 53823975HCID 53823975, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(Cyanoimino)thiazolidine (6.35 g, 49.9 mmol), prepared by the procedure of Neidlein and Reuter, Arch. Pharm. (Weinheim, Ger.) 305, 731 (1972), was added to a suspension of sodium hydride (2.04 g, 51 mmol, pre-washed with hexane)in dimethylformamide (100 mL) at ambient temperature, resulting in heat and gas evolution. After stirring the mixture 30 minutes, tert-butyl bromoacetate (10.0 g, 51.3 mmol) was added and the resulting mixture was stirred 2.5 hours at ambient temperature. After removing the solvent in vacuo, the residue was partitioned between saturated sodium bicarbonate and methylene chloride and the aqueous phase extracted with additional methylene chloride (2×). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. Subsequent recrystallization from methylene chloride/hexane (1:4) afforded 9.04 g (75%) of the title compound as a white crystalline solid. m.p. 143°-144° C. TLC (ethyl acetate) Rf =0.44. 1H NMR (CDCl3, 300 MHz) d 1.48 (s, 9H), 1.48 (s, 9H), 3.43 (t, 2H), 3.98 (t, 2H), 4.08 (s, 2H). MS (DCl/NH3) m/e 242 (M+H)+. Anal calcd for C10H15N3O2S.0.25 H2O: C, 48.86; H, 6.36; N, 17.09. Found: C, 48.71; H, 5.98; N, 16.93.

Workup

  1. customresulting
  2. temperaturein heat
  3. additionwas added
  4. customAfter removing the solvent in vacuo
  5. customthe residue was partitioned between saturated sodium bicarbonate and methylene chloride
  6. extractionthe aqueous phase extracted with additional methylene chloride (2×)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customSubsequent recrystallization from methylene chloride/hexane (1:4)

Sources & evidence

ORD record
ord-217f37f6c30945caaefda0304d35a67a
Source dataset
uspto-grants-1994_07
Patent number
US05326776

Reaction notes

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