P-Phenylenediamine → HCID 24772584, compound

HRID 1676845Notes

Reaction equation

HRID 1676845 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.[C:9](=[O:12])(O)[O-].[Na+].[CH2:14]([O:21][CH2:22][C:23](Cl)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)(=O)C>[CH2:14]([O:21][CH2:22][C:23]([NH:7][C:4]1[CH:5]=[CH:6][C:1]([NH:8][C:9](=[O:12])[CH2:22][O:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:2][CH:3]=1)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7814P-PhenylenediamineHCID 177085Benzyloxyacetyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 24772584HCID 24772584, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1,4-phenylenediamine (10 grams, 92.47 mmol), sodium bicarbonate (15.46 grams, 184.07 mmol) in ethyl acetate (100 mL) at 0° C. is added benzyloxy acetyl chloride (23.19 grams, 125.71 mmol) drop wise. The reaction mixture is stirred at room temperature for 10 hours. The solids are filtered, and the ethyl acetate layer is washed with 5% sodium bicarbonate solution (2×25 mL), water (2×25 mL), dried over sodium sulfate, and distilled to get crude 3, which can be purified by suitable solvent.

Workup

  1. filtrationThe solids are filtered
  2. washthe ethyl acetate layer is washed with 5% sodium bicarbonate solution (2×25 mL), water (2×25 mL)
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled
  5. customto get crude 3, which
  6. customcan be purified by suitable solvent

Sources & evidence

ORD record
ord-3e860fbde7344fef98efe8e2c6967d83
Source dataset
uspto-grants-2011_08
Patent number
US08007526B2

Reaction notes

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