Acetic Acid → HCID 22388450, compound

HRID 1699862Notes

Reaction equation

HRID 1699862 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-a3809d473fe0467cb6fe0ed7b72893c4
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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