Ethyl benzoylformate → HCID 178527200, compound

HRID 1285370Notes

Reaction equation

HRID 1285370 reaction equation
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].[Na].[C:7]1([C:13](=O)[C:14](OCC)=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C>[OH:15][C:14]1[C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][S:1](=[O:3])(=[O:2])[N:4]=1

Participants

5

Reactant 3

HCID 15349Ethyl benzoylformateHCID 82267SulfamideHCID 5360545Sodium

Product 1

HCID 178527200HCID 178527200, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Sulfamide (4.8 g, 50 mmoles) in ethanol (90 ml) was added slowly with stirring under nitrogen to a solution of sodium (1.15 g, 50 mmoles) dissolved in ethanol (35 ml). The suspension was stirred for 15 minutes at room temperature and then ethyl phenylglyoxylate (8.9 g, 50 mmoles) in ethanol (15 ml) was added. After stirring 15 minutes, the mixture was refluxed overnight and concentrated under vacuum. The residue was suspended in diethyl ether, filtered and the collected solid dissolved in water (25 ml). Acidification with hydrochloric acid precipitated the product which was collected by filtration, washed with water and recrystallized from a mixture of acetonitrile (12 ml) and toluene (8 ml) to obtain 4.2 g (40%) of the title compound, mp 202°-4°. Nmr (DMSO-d6): δ 7.29-7.89 (m, 3H), 8.19-8.49 (m, 2H).

Workup

  1. stirringAfter stirring 15 minutes
  2. temperaturethe mixture was refluxed overnight
  3. concentrationconcentrated under vacuum
  4. filtrationfiltered
  5. dissolutionthe collected solid dissolved in water (25 ml)
  6. customAcidification with hydrochloric acid precipitated the product which
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customrecrystallized from a mixture of acetonitrile (12 ml) and toluene (8 ml)

Sources & evidence

ORD record
ord-515a7f7412a14b2d9b848a546b94632d
Source dataset
uspto-grants-1986_01
Patent number
US04567191

Reaction notes

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