Dimethylformamide → HCID 66782073, compound

HRID 1360148Notes

Reaction equation

HRID 1360148 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH3:19])[CH2:14][O:13][CH2:12][C:11](N(N=O)C)=[N:10]2)=[CH:5][CH:4]=1.CN(C)C=O.CC(C)([O-])C.[K+].[N+:31]([CH3:34])([O-:33])=[O:32]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([CH3:19])[CH2:14][O:13][CH2:12]/[C:11](=[CH:34]/[N+:31]([O-:33])=[O:32])/[NH:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6375NitromethaneHCID 23665647Potassium tert-butoxideHCID 87149360HCID 87149360, compound

Product 1

HCID 66782073HCID 66782073, compound

Procedure

A mixture of 100 mmol of [5-(4-methoxyphenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-N-nitroso-N-methylamine, 200 ml of N,N-dimethylformamide, 50 ml of nitromethane and 115 mmol of potassium tert-butoxide is stirred at room temperature for 15 minutes. It is quenched by adding 20 ml of glacial acetic acid and diluted with dichloromethane and water. The organic phase is separated off, washed with water, dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60F).

Workup

  1. customIt is quenched
  2. additionby adding 20 ml of glacial acetic acid
  3. additiondiluted with dichloromethane and water
  4. customThe organic phase is separated off
  5. washwashed with water
  6. dry with materialdried with sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-1a060d8eeff14c21a9f8f88cea0c26f7
Source dataset
uspto-grants-2011_02
Patent number
US07879847B2

Reaction notes

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