Sulfuric Acid → HCID 20451897, compound

HRID 1463161Notes

Reaction equation

HRID 1463161 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[NH2:11].S(=O)(=O)(O)[OH:13].[OH-].[Na+]>O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:13])[NH2:10])=[CH:4][C:3]=1[NH2:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 14891906HCID 14891906, compound

Product 1

HCID 20451897HCID 20451897, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.03 g. of 1,2-diamino-4-cyanomethylbenzene (1.03 g.) was slowly added concentrated sulphuric acid (7 ml.). The mixture was heated at 90° for 90 minutes, then poured onto 50 ml. of water and ice and adjusted to pH 8 with NaOH. The precipitate which formed on cooling was discarded and the aqueous phase was concentrated to drynes. The residue was extracted with acetone, the extracts were concentrated and chromatographed on silica gel using CH2Cl2 /MeOH 9:1 to 8:2 v/v to give 1,2-diamino-4-carbamoylmethylbenzene (0.65 g.) which was used without further purification.

Workup

  1. temperatureThe mixture was heated at 90° for 90 minutes
  2. additionpoured onto 50 ml
  3. customThe precipitate which formed
  4. temperatureon cooling
  5. concentrationthe aqueous phase was concentrated to drynes
  6. extractionThe residue was extracted with acetone
  7. concentrationthe extracts were concentrated
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-c3ff2f557df14504940415bd5b70f12f
Source dataset
uspto-grants-1984_07
Patent number
US04463173

Reaction notes

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