Sodium hydride → HCID 131728532, compound

HRID 1695296Notes

Reaction equation

HRID 1695296 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:26])[C:6]1[CH:11]=[C:10]([CH3:12])[C:9](Br)=[C:8]([S:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[NH2:25])(=[O:16])=[O:15])[CH:7]=1>CN(C)C=O>[CH3:3][O:4][C:5]([C:6]1[CH:11]=[C:10]([CH3:12])[C:9]2[NH:25][C:19]3[C:20]([Cl:24])=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][S:14](=[O:16])(=[O:15])[C:8]=2[CH:7]=1)=[O:26]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67246082HCID 67246082, compound

Product 1

HCID 131728532HCID 131728532, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.234 g, 5.07 mmol) was added in portions to a stirred solution of Example 37d (0.785 g, 1.69 mmol) in dry dimethylformamide (10 mL) at 0° C. The reaction mixture was stirred for 0.5 h. Excess sodium hydride was destroyed using methanol (5 mL). The reaction mixture was diluted with cold water (100 mL), the solid separated was filtered, crystallized using ethyl acetate/pet. ether 60-80° C. to obtain the title compound. Yield: 0.409 g, (64.10%); 1H NMR (DMSO-d6, 300 MHz): δ 2.65 (s, 3H, CH3), 3.90 (s, 3H, OCH3), 5.15 (s, 2H, CH2), 7.25 (t, 1H, Ar), 7.65 (d, 1H, Ar), 7.75 (d, 1H, Ar), 7.85 (s, 1H, NH), 8.05 (s, 1H, Ar), 8.35 (s, 1H, Ar); MS: m/e (El) 351 (M+).

Workup

  1. customExcess sodium hydride was destroyed
  2. additionThe reaction mixture was diluted with cold water (100 mL)
  3. customthe solid separated
  4. filtrationwas filtered
  5. customcrystallized
  6. customethyl acetate/pet. ether 60-80° C.

Sources & evidence

ORD record
ord-aab19a47f7b841af85f0ceddef39b9c5
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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