Sodium Methoxide → HCID 21340579, compound

HRID 2184715Notes

Reaction equation

HRID 2184715 reaction equation
C[O-].[Na+].C([O:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([S:24]([NH2:27])(=[O:26])=[O:25])[C:13]2[C:18]([C:19]=1[Br:20])=[CH:17][CH:16]=[CH:15][C:14]=2[N+:21]([O-:23])=[O:22])(=O)C>CO>[Br:20][C:19]1[C:18]2[C:13](=[C:14]([N+:21]([O-:23])=[O:22])[CH:15]=[CH:16][CH:17]=2)[C:12]([S:24]([NH2:27])(=[O:25])=[O:26])=[CH:11][C:10]=1[CH2:9][CH2:8][OH:7]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 22457535HCID 22457535, compound

Product 1

HCID 21340579HCID 21340579, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium methoxide in methanol (23.7 mL of a 0.5M solution, 11.8 mmol) was added to a suspension of 3-(2-acetoxy-ethyl)-4-bromo-8-nitro-naphthalene-1-sulfonamide (4.70 g, 11.3 mmol) in methanol (33 mL). The mixture was stirred under a nitrogen atmosphere at room temperature for 90 minutes, then concentrated under vacuum to approximately half volume, diluted with ethyl acetate (200 mL), and washed with 2N hydrochloric acid. The organic solution was washed with water (100 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and left to stand at room temperature. The organic solution deposited a solid which was collected by filtration, washed with ethyl acetate (2×15 mL), and vacuum dried to give the title compound (1.78 g). Additional product (1.88 g) was obtained from the mother liquors after concentration under vacuum and crystallization from diethyl ether.

Workup

  1. concentrationconcentrated under vacuum to approximately half volume
  2. additiondiluted with ethyl acetate (200 mL)
  3. washwashed with 2N hydrochloric acid
  4. washThe organic solution was washed with water (100 mL) and brine (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. waitleft
  8. customto stand at room temperature
  9. filtrationwas collected by filtration
  10. washwashed with ethyl acetate (2×15 mL), and vacuum
  11. customdried

Sources & evidence

ORD record
ord-51e0f679470b4bf6a500840317de3567
Source dataset
uspto-grants-2002_06
Patent number
US06399597B1

Reaction notes

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