Sodium hydride → HCID 18385404, compound

HRID 2298034Notes

Reaction equation

HRID 2298034 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH3:22])[CH:14]=2)[N:10]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][CH:24]=2)[C:9]1=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:34][CH2:35][CH2:36][CH2:37][N:38]1[C:42](=[O:43])[C:41]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:40]2[C:39]1=[O:48].[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH3:22])[CH:14]=2)[N:10]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH2:34][CH2:35][CH2:36][CH2:37][N:38]3[C:42](=[O:43])[C:41]4[C:40](=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:39]3=[O:48])[CH:24]=2)[C:9]1=[O:32])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 93575N-(4-Bromobutyl)phthalimideHCID 18385439HCID 18385439, compound

Product 1

HCID 18385404HCID 18385404, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of step e) (0.034 g, 0.080 mmol), N-(4-bromobutyl)phthalimide (0.028 g, 0.10 mmol) and sodium hydride (95%, 0.0024 g, 0.10 mmol) was dissolved in dry DMF (0.5 ml). After stirring at room temperature for 1.5 hour HPLC shows complete reaction. The reaction was quenched by addition of aqueous acetic acid (1 M, 2 ml) and ethyl acetate (2 ml). The phases were separated and the organic phase washed with water (1×2 ml). Solvent removal followed by chromatographic purification on silica, eluting with heptane—ethyl acetate (20:80), furnished the sub-title product (0.019 g, 38%) as a slightly brown solid.

Workup

  1. customreaction
  2. customThe reaction was quenched by addition of aqueous acetic acid (1 M, 2 ml) and ethyl acetate (2 ml)
  3. customThe phases were separated
  4. washthe organic phase washed with water (1×2 ml)
  5. customSolvent removal
  6. customfollowed by chromatographic purification on silica
  7. washeluting with heptane—ethyl acetate (20:80)

Sources & evidence

ORD record
ord-4cb5232689854540964f110cf1425260
Source dataset
uspto-grants-2002_12
Patent number
US06492409B1

Reaction notes

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