Dimethylhydantoin → HCID 68563813, compound

HRID 1023491Notes

Reaction equation

HRID 1023491 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:11])[NH:8][C:7](=[O:9])[NH:6][C:5]1=[O:10].[Br:12][CH2:13][CH2:14][N+:15]([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C>[Br-:12].[CH3:3][C:4]1([CH3:11])[C:5](=[O:10])[N:6]([CH2:13][CH2:14][N+:15]([CH3:18])([CH3:17])[CH3:16])[C:7](=[O:9])[NH:8]1

Participants

5

Reactant 3

HCID 6491DimethylhydantoinHCID 176902-bromoethyl(trimethyl)azaniumHCID 24758Sodium hydride

Product 1

HCID 68563813HCID 68563813, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of NaH (60% in mineral oil, 1.75 g) in DMF (25 mL) at 5° C. was added 5,5-dimethyl hydantoin (5 g, 39.0 mmol, 1 eq) and the reaction was stirred for 30 min. Added (2-bromoethyl)trimethylammonium (9.6 g, 39.0 mmol, 1 eq) at that temperature and the reaction was heated to 50° C., while stirring overnight. Reaction was cooled to room temperature and the product crashed out of solution as a white solid, which was cooled to 5° C., filtered and washed with cold DMF (30 mL). Purified by prep-HPLC (gradient from 5% to 95% MeOH in H2O; 20 mL/min flow rate; C18 Restek column) to yield the desired product. Yield: 778 mg (7%). 1H-NMR (400 MHz, D2O) δ 4.005 (t, J=7.6 Hz, 2H), 3.643 (t, J=7.6 Hz, 6H), 3.238 (s, 9H), 1.441 (s, 6H) LCMS—[M] m/z 214.05

Workup

  1. stirringwhile stirring overnight
  2. customReaction
  3. temperaturewas cooled to 5° C.
  4. filtrationfiltered
  5. washwashed with cold DMF (30 mL)
  6. customPurified by prep-HPLC (gradient from 5% to 95% MeOH in H2O; 20 mL/min flow rate; C18 Restek column)

Sources & evidence

ORD record
ord-5d3d25ca54364a418cfd1ebabb914d6c
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

Loading…