Sodium Methoxide → HCID 21340579, compound

HRID 1604264Notes

Reaction equation

HRID 1604264 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, compound

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 oganic 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 comound (1.78 g). Additional poduct (1.88g) 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 oganic 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
  12. customto give the title comound (1.78 g)
  13. customAdditional poduct (1.88g) was obtained from the mother liquors
  14. concentrationafter concentration
  15. customunder vacuum and crystallization from diethyl ether

Sources & evidence

ORD record
ord-16032bcdc5eb4ec6a12ef6eac7b435e2
Source dataset
uspto-grants-1999_11
Patent number
US05994345

Reaction notes

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