Acetic Acid → HCID 22388450, compound

HRID 1072841Notes

Reaction equation

HRID 1072841 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22].S(=O)(=O)(O)O.C(O)(=O)C.[N:32]([O-])=O.[Na+]>O1CCCC1.O>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[CH2:14][N:13]1[C:3]2[CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:11]=[CH:12][C:2]=2[N:1]=[N:32]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 22387919HCID 22387919, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22388450HCID 22388450, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-amino-3-(2,4-dichlorobenzylamino)benzoate (0.89 g), concentrated sulfuric acid (1.0 g) were stirred in a mixed solvent of acetic acid (20 ml), water (10 ml) and tetrahydrofuran (20 ml). Sodium nitrite (3.0 g) was added thereto, and the mixture was stirred at room temperature for 30 min. The solvent was distilled away, and water was added to separate the toluene layer. The mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate. The toluene layer was concentrated to give the objective compound (0.64 g) as a crude product.

Workup

  1. distillationThe solvent was distilled away
  2. additionwater was added
  3. customto separate the toluene layer
  4. washThe mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate
  5. concentrationThe toluene layer was concentrated

Sources & evidence

ORD record
ord-2f80f5c8b3154de596b77e3c57d3589e
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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