Acetonitrile → 3-Methylureido-1-(p-sulfophenyl)-5-pyrazolone Triethylamine Salt

HRID 1449073

Reaction equation

HRID 1449073 reaction equation
[C:1](#[N:3])[CH3:2].[C:4](OOC(CC)(N)C)(=[O:7])[CH:5]=C.[CH3:15][N:16]=[C:17]=[O:18].[S:19]([C:23]1[CH:28]=[CH:27][C:26]([NH:29][NH2:30])=[CH:25][CH:24]=1)([OH:22])(=[O:21])=[O:20]>C(O)(=O)C.C(N(CC)CC)C.CO>[CH2:1]([N:3]([CH2:23][CH3:24])[CH2:4][CH3:5])[CH3:2].[CH3:15][NH:16][C:17](=[O:18])[NH:3][C:1]1[NH:30][N:29]([C:26]2[CH:25]=[CH:24][C:23]([S:19]([OH:22])(=[O:20])=[O:21])=[CH:28][CH:27]=2)[C:4](=[O:7])[CH:2]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 12228Methyl IsocyanateHCID 668254-Hydrazinobenzenesulfonic acidHCID 86736826Ethylbeta-amino-beta-ethoxy acrylate

Product 1

HCID 867368293-Methylureido-1-(p-sulfophenyl)-5-pyrazolone Triethylamine Salt

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

Into 30 ml of acetonitrile was dissolved 15.9 g of ethylβ-amino-β-ethoxy acrylate, and 6 g of methyl isocyanate was added thereto. The resulting mixture was allowed to stand at room temperature for 2 days. Into a mixed solution of 50 ml of methanol, 50 ml of triethylamine and 50 ml of glacial acetic acid there was dissolved 18.8 g of p-sulfophenyl hydrazine, into which was then slowly dropped the above solution in which the esterification reaction had been completed. The solution so obtained was allowed to stand at room temperature for 4 days, whereupon crystals precipitated. These crystals were combined and washed with acetonitrile and then recrystallized from ethanol; thus, 31 g of pale yellow plate-like crystals of the objective compound of a melting point of 248° to 250° C. was obtained.

Workup

  1. additionwas added
  2. additioninto which was then slowly dropped the above solution in which
  3. customthe esterification reaction
  4. customThe solution so obtained
  5. waitto stand at room temperature for 4 days, whereupon crystals
  6. customprecipitated
  7. washwashed with acetonitrile
  8. customrecrystallized from ethanol
  9. customthus, 31 g of pale yellow plate-like crystals of the objective compound of a melting point of 248° to 250° C. was obtained

Sources & evidence

ORD record
ord-a7b4b3133e224ba994bf6ff2500ed112
Source dataset
uspto-grants-1980_02
Patent number
US04188489

Linked notes

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