Carbamimidic acid, methyl ester, sulfate (1:1) → HCID 13975859, compound

HRID 1722403Notes

Reaction equation

HRID 1722403 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:19](=O)[CH3:20])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:22][O:23][C:24]([NH2:26])=[NH:25].OS(O)(=O)=O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:22][O:23][C:24]1[NH:26][C:19]([CH3:20])=[C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:25]=1

Participants

5

Reactant 3

HCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 516892Sodium BicarbonateHCID 56996553HCID 56996553, compound

Product 1

HCID 13975859HCID 13975859, compoundYield 122.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid, t-butyl ester (6.80 g, 23.3 mmol), o-methylisourea hydrogen sulfate (5.22 g, 30.3 mmol), and sodium bicarbonate (5.87 g, 69.9 mmol) in dimethylformamide (35 ml) was stirred at room temperature overnight under argon. After 23 hours at room temperature, the reaction was heated at 60° C. (oil bath) for 5.5 hours. It was then partitioned between ethyl acetate and 5% sodium bicarbonate. The organic phase was washed several times with water, washed with saturated sodium chloride, and dried over potassium carbonate. Evaporation gave crude title compound as a light brown oil (9.93 g).

Workup

  1. waitAfter 23 hours at room temperature
  2. temperaturethe reaction was heated at 60° C. (oil bath) for 5.5 hours
  3. customIt was then partitioned between ethyl acetate and 5% sodium bicarbonate
  4. washThe organic phase was washed several times with water
  5. washwashed with saturated sodium chloride
  6. dry with materialdried over potassium carbonate
  7. customEvaporation

Sources & evidence

ORD record
ord-b06e8931c8234e9489d4078c47805477
Source dataset
uspto-grants-1989_08
Patent number
US04855301

Reaction notes

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