Dichloromaleic anhydride → HCID 86139785, compound

HRID 1773065Notes

Reaction equation

HRID 1773065 reaction equation
C([O-])C.[Na+].[Cl:5][C:6]1[C:7]([O:9][C:10](=[O:13])[C:11]=1[Cl:12])=O.Cl.[CH3:15][O:16][NH2:17]>C(O)(=O)C>[Cl:12][C:11]1[C:10](=[O:13])[N:17]([O:16][CH3:15])[C:7](=[O:9])[C:6]=1[Cl:5]

Participants

5

Reactant 3

HCID 70728Dichloromaleic anhydrideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 2723922Sodium ethoxide

Product 1

HCID 86139785HCID 86139785, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

At room temperature 3.6 g (52.9 mmol) sodium ethanolate were added to a mixture of 5.6 g (33.5 mmol) 2.3-dichloro maleic anhydride and 4.6 g (55.1 mmol) methoxyamine hydrochloride in 50 ml of acetic acid. The reaction mixture was stirred 16 hours at room temperature and then poured into an ice/water mixture. An insoluble solid crystallized out which was filtered off and washed with water. Then this solid was redissolved in ethyl acetate. the solution was dried over magnesium sulfate and evaporated. 4.5 g (68% of theory) of the title compound were obtained as a light colored solid. 1H-NMR (CDCl3. δ in ppm): 4.0 (s. 3H).

Workup

  1. customAn insoluble solid crystallized out which
  2. filtrationwas filtered off
  3. washwashed with water
  4. dissolutionThen this solid was redissolved in ethyl acetate
  5. dry with materialthe solution was dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-f037b6a3b849492589b7803984d13c30
Source dataset
uspto-grants-2016_02
Patent number
US09253980B2

Reaction notes

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