Acetic Acid → 5-Amino-2-[(4-amino-2-carbamoylphenyl)disulfanyl]benzamide

HRID 3258Notes

Reaction equation

HRID 3258 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:13][S:14][C:15]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:16]=2[C:17]([NH2:19])=[O:18])=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10])([O-])=O.C(O)(=O)C.[OH-].[Na+]>O>[NH2:24][C:21]1[CH:22]=[CH:23][C:15]([S:14][S:13][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:12][C:8]=2[C:9]([NH2:11])=[O:10])=[C:16]([CH:20]=1)[C:17]([NH2:19])=[O:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 15284590HCID 15284590, compound

Product 1

HCID 4629255-Amino-2-[(4-amino-2-carbamoylphenyl)disulfanyl]benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,2'-Dithiobis(5-nitrobenzamide) (2.6 g, 7.0 mmol) was added portion-wise to a refluxing slurry of reduced iron (8.7 g) in 65 mL of water containing 0.1 mL of acetic acid. The resulting slurry was heated at reflux for 2.0 hours, then cooled to room temperature. The slurry was made strongly basic (pH 11) by the addition of 14 mL of 1N NaOH. The alkaline mixture was filtered, and acetic acid was added to the solution to adjust the pH to 7.0. While bubbling oxygen into the solution, a pH=6-7 was maintained with the addition of acetic acid. A solid gradually formed as the pH begins to stabilize. The product (1.1 g) was recovered by filtration, mp 188°-190° C.

Workup

  1. temperatureThe resulting slurry was heated
  2. temperatureat reflux for 2.0 hours
  3. filtrationThe alkaline mixture was filtered
  4. additionacetic acid was added to the solution
  5. customWhile bubbling oxygen into the solution
  6. temperaturea pH=6-7 was maintained with the addition of acetic acid
  7. customA solid gradually formed as the pH
  8. filtrationThe product (1.1 g) was recovered by filtration, mp 188°-190° C.

Sources & evidence

ORD record
ord-31a8839874394a4985cf9f31ccc798f0
Source dataset
uspto-grants-1998_03
Patent number
US05733921

Reaction notes

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