Acetic Anhydride → HCID 18965348, compound

HRID 2226458Notes

Reaction equation

HRID 2226458 reaction equation
C[O-].[Na+].Cl.[NH2:5]O.[CH2:7]([N:14]1[CH2:18][CH2:17][CH:16]([CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:29]#[N:30])[CH:27]=3)[NH:22][CH:21]=2)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:31]([O:34]C(=O)C)(=O)[CH3:32].[OH-].[Na+]>CO.O>[CH2:7]([N:14]1[CH2:18][CH2:17][CH:16]([CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:29]4[N:5]=[C:31]([CH3:32])[O:34][N:30]=4)[CH:27]=3)[NH:22][CH:21]=2)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 18965360HCID 18965360, compound

Product 1

HCID 18965348HCID 18965348, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution containing 12.7 mmol of sodium methoxide in 5 ml of methanol is added to a solution containing 12.7 mmol of hydroxylamine hydrochloride in 15 ml of methanol. The mixture is stirred for one hour at room temperature. After filtration of the precipitate, 5.7 mmol of the compound of Example 14 are added to the filtrate and the combined mixture is brought to reflux for 48 hours. After evaporation of the solvent, the brown solid obtained is mixed with 10 ml of acetic anhydride. The combined mixture is heated for 24 hours at 80° C. After hydrolysis with water, the combined mixture is brought to pH=12 using 2N sodium hydroxide solution. After extraction with dichloromethane, drying and evaporation, the expected product is obtained after purification of the residue by chromatography on a silica column, using a dichloromethane/methanol/aqueous ammonia (95/5/0.5) mixture as eluent.

Workup

  1. additionis added to a solution
  2. additionare added to the filtrate
  3. temperatureto reflux for 48 hours
  4. customAfter evaporation of the solvent
  5. customthe brown solid obtained
  6. temperatureThe combined mixture is heated for 24 hours at 80° C
  7. extractionAfter extraction with dichloromethane
  8. customdrying
  9. customevaporation

Sources & evidence

ORD record
ord-897dd9c612614086a09fca20f81b410b
Source dataset
uspto-grants-1994_09
Patent number
US05348968

Reaction notes

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