HCID 21941239, compound → HCID 178499399, compound

HRID 2216246Notes

Reaction equation

HRID 2216246 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=1[NH2:16])(=O)C.[N:17]([O-])=O.[Na+]>C(O)(=O)C.O.C(OCC)(=O)C>[NH:4]1[C:5]2[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[N:16]=[N:17]1

Participants

6

Reactant 2

HCID 21941239HCID 21941239, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178499399HCID 178499399, compoundYield 71.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-acetamido-3-aminophenylacetate (77 g, 0.373 mol) was taken up in a mixture of acetic acid (210 ml) and water (210 ml) and cooled to below 5° C. A solution of sodium nitrite (38.63 g, 0.559 mol) in water (200 ml) was added dropwise, and once the addition was complete the mixture was stirred for 4 hours, warming slowly to room temperature. The mixture was diluted with ethyl acetate and the insoluble material removed by filtration. The filtrate was washed with brine, dried over anhydrous magnesium sulfate, filtered and the solvent evaporated in vacuo, to give a viscous residue (51 g) which was then dissolved in a solution of methanol (400 ml) previously saturated with hydrogen chloride and the mixture stirred for 2 hours. The solvent was removed in vacuo, the residue taken up in water, neutralised with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo to afford methyl 5-benzotriazoleacetate (35 g) as a reddish liquid which crystallised on standing.

Workup

  1. temperaturecooled to below 5° C
  2. additiononce the addition
  3. customthe insoluble material removed by filtration
  4. washThe filtrate was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-8dd2751e43434c598fe285bc37c9a020
Source dataset
uspto-grants-2006_09
Patent number
US07112553B1

Reaction notes

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