Toluene → 4-Amino-3-chloro-5-methoxyiminomethylbenzoyl chloride

HRID 370024Notes

Reaction equation

HRID 370024 reaction equation
[NH2:1][C:2]1[C:10]([CH:11]=[N:12][O:13][CH3:14])=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[Cl:15].C1(C)C=CC=CC=1.S(Cl)([Cl:25])=O>CN(C)C=O>[NH2:1][C:2]1[C:10]([CH:11]=[N:12][O:13][CH3:14])=[CH:9][C:5]([C:6]([Cl:25])=[O:7])=[CH:4][C:3]=1[Cl:15]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 540991344-Amino-3-chloro-5-methoxyiminomethylbenzoic acid

Product 1

HCID 544540514-Amino-3-chloro-5-methoxyiminomethylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

In a 5-liter three-necked round-bottomed flask was placed 180 g of the previously prepared 4-amino-3-chloro-5-methoxyiminomethylbenzoic acid, 2 l of toluene, 3 mL of dimethylformamide and 104 g (64 mL) of thionyl chloride. The resulting mixture was heated at 70° C. for 2 hours, filtered while hot and the solvent removed using a rotary evaporator yielding 178.1 g of the expected 4-amino-3-chloro-5-methoxyiminomethylbenzoyl chloride.

Workup

  1. customIn a 5-liter three-necked round-bottomed flask was placed
  2. filtrationfiltered while hot and the solvent
  3. customremoved
  4. customa rotary evaporator

Sources & evidence

ORD record
ord-d37d0d004e6b4141a4e103e2f0b98b0f
Source dataset
uspto-grants-2000_10
Patent number
US06140362

Reaction notes

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