Ammonia → HCID 15767242, compound

HRID 1421382Notes

Reaction equation

HRID 1421382 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]([C:11]([O:13][CH3:14])=[O:12])[OH:10].[C:15]([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O.N>CC(C)=O.C(Cl)Cl>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[N:9]([C:11]([O:13][CH3:14])=[O:12])[O:10][CH3:15]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 15767241HCID 15767241, compound

Product 1

HCID 15767242HCID 15767242, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.4 g (7.2 mmol) of N-(2,6-dimethylphenyl)-N-methoxycarbonyl-hydroxylamine (Example 1a), 1.3 g (9 mmol) of K2CO3 and 10 g (8 mmol) of dimethyl sulfate in 10 ml of acetone is stirred overnight at room temperature. The reaction mixture is then diluted with CH2Cl2 and stirred with dilute NH3 solution. The phases are then separated and the organic phase is extracted another twice with water. The organic phase is dried over MgSO4 and evaporated down, and the residue is purified by column chromatography with mixtures of cyclohexane and ethyl acetate. There is obtained 1.2 g (6 mmol=83%) of the title compound as a colorless solid (mp=81° C.).

Workup

  1. customThe phases are then separated
  2. extractionthe organic phase is extracted another twice with water
  3. dry with materialThe organic phase is dried over MgSO4
  4. customevaporated down
  5. customthe residue is purified by column chromatography with mixtures of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-eab9fd3ad404495497d321290aded48d
Source dataset
uspto-grants-2000_06
Patent number
US06075148

Reaction notes

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