Ethanol → HCID 70213064, compound

HRID 2270138Notes

Reaction equation

HRID 2270138 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([S:12](=[O:19])(=[O:18])[NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1.[N:20]([O-:22])=[O:21].[Na+].[C:24]([O-:27])(=[O:26])C.[Na+].[N+:29]([CH2:32]C(OCC)=O)([O-])=O.[CH2:38](O)[CH3:39]>Cl.O>[C:14]([NH:13][S:12]([C:4]1[CH:3]=[C:2]([N:1]([C:24]([O:27][CH2:38][CH3:39])=[O:26])[N:29]=[CH:32][N+:20]([O-:22])=[O:21])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])(=[O:19])=[O:18])([CH3:16])([CH3:15])[CH3:17]

Participants

8

Reactant 5

HCID 702EthanolHCID 69379Ethyl nitroacetateHCID 517045Sodium AcetateHCID 10946074methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoateHCID 23668193Sodium Nitrite

Product 1

HCID 70213064HCID 70213064, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

5.7 g (0.02 mol) of methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate are suspended in a mixture of 30 ml of conc. HCl and 36 ml of water. At 0-50° C., a solution of 1.5 g (0.022 mol) of sodium nitrite in 9 ml of water is added dropwise. The few undissolved components are filtered off cold, and the cold diazonium salt solution is slowly poured, at 5-10° C., into a mixture of 8.9 g (0.11 mol) of sodium acetate, 16 ml of water, 60 ml of ethanol and 2.7 g (0.02 mol) of ethyl nitroacetate. Stirring is continued at 0° C. for 2 h and the mixture is left to stand at this temperature for 15 h. The mixture is filtered off and the solid is washed with water and dried under reduced pressure, giving 5.2 g (60% of theory) of methyl 2-(N-tert-butylsulfamoyl)-4-(ethoxycarbonylnitromethylenehydrazino)benzoate of m.p. 142-145° C.

Workup

  1. filtrationThe few undissolved components are filtered off cold
  2. waitthe mixture is left
  3. waitto stand at this temperature for 15 h
  4. filtrationThe mixture is filtered off
  5. washthe solid is washed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-14973849024c40909c96f3d5c191a3a3
Source dataset
uspto-grants-2001_12
Patent number
US06331506B1

Reaction notes

Loading…