Sodium hydride → HCID 13000267, compound

HRID 495963Notes

Reaction equation

HRID 495963 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19].[H-].[Na+]>>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]2[C:3](=[O:2])[NH:19][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][C:5]=2[CH:6]=1

Participants

3

Reactant 2

HCID 24758Sodium hydrideHCID 21339496HCID 21339496, compound

Product 1

HCID 13000267HCID 13000267, compound

Procedure

A solution of 1-2 (47.80 g, 174.9 mmol) in TBF (1 L) was treated with sodium hydride (7.430 g of 60% in oil, 185.7 mmol) in portions and stirred at room temperature for 3 days. The reaction was quenched with aqueous ammonium chloride and extracted three times with diethyl ether. The combined organic extracts were washed with brine and dried (Na2SO4). The solvent was removed in vacuo to afford the crude product 1-3. Recrystallization from ethyl acetate gave 1-3 as white crystals.

Workup

  1. customThe reaction was quenched with aqueous ammonium chloride
  2. extractionextracted three times with diethyl ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed in vacuo
  6. customto afford the crude product 1-3
  7. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-f86a39801c2740cd996145acb9f318a0
Source dataset
uspto-grants-2005_09
Patent number
US06943156B2

Reaction notes

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