Hydroxyamine hydrochloride → HCID 72440634, compound

HRID 32084Notes

Reaction equation

HRID 32084 reaction equation
CC([O-])=O.[Na+].[CH3:6][O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[C:18](=O)[CH2:17][S:16](=[O:21])(=[O:20])[N:15]([CH3:22])[C:14]=2[CH:23]=1)=[O:9].Cl.[NH2:25][OH:26]>CCO>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[C:18](=[N:25][OH:26])[CH2:17][S:16](=[O:21])(=[O:20])[N:15]([CH3:22])[C:14]=2[CH:23]=1)=[O:9]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 2778961Methyl 1-methyl-2,2,4-trioxo-1,2,3,4-tetrahydro-2,1-benzothiazine-7-carboxylate

Product 1

HCID 72440634HCID 72440634, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaOAc (3.66 g, 44.5 mmol) was added to an EtOH (100 mL) solution of 1-methyl-2,2,4-trioxo-1,2,3,4-tetrahydro-2λ6-benzo[c][1,2]thiazine-7-carboxylic acid methyl ester (4.00 g, 14.8 mmol) and hydroxylamine hydrochloride (1.55 g, 22.3 mmol). After heating at reflux for 4 days, it was evaporated, diluted with CH2Cl2 (400 mL), washed with H2O, dried over MgSO4, filtered, and concentrated in vacuo. Crystallization from MeOH provided the title compound. MS (−APCI, m/z): 283 (M−H)−.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 4 days
  3. customit was evaporated
  4. additiondiluted with CH2Cl2 (400 mL)
  5. washwashed with H2O
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customCrystallization from MeOH

Sources & evidence

ORD record
ord-6163bbd45cf44501bc069bd359296eb0
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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