Water → HCID 13259763, compound

HRID 2295954Notes

Reaction equation

HRID 2295954 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[N+:12]([C:15]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:26]=2[Cl:35])=[CH:20][C:16]=1[C:17](Cl)=[O:18])([O-:14])=[O:13].O>CN(C)C=O>[N+:12]([C:15]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][C:26]=2[Cl:35])=[CH:20][C:16]=1[C:17]([N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6])=[O:18])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 6809PhthalimideHCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chloride

Product 1

HCID 13259763HCID 13259763, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The N-potassium salt of phthalimide (4.63 grams; 0.025 mole) dissolved in dimethylformamide (50 ml) was charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. 2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)benzoyl chloride (9.5 grams; 0.025 mole) was added and the reaction mixture was stirred at room temperature overnight. After this time the mixture was poured into water and was thereafter extracted with toluene. The toluene extract was evaporated to dryness leaving a dark reddish solid. This solid was recrystallized from toluene to yield the desired product N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)benzoyl]phthalimide as a white powder melting at 160° C.

Workup

  1. additionwas charged into a glass reaction vessel
  2. customequipped with a mechanical stirrer
  3. extractionwas thereafter extracted with toluene
  4. extractionThe toluene extract
  5. customwas evaporated to dryness
  6. customleaving a dark reddish solid
  7. customThis solid was recrystallized from toluene

Sources & evidence

ORD record
ord-778fda17ff40410a82d2e1376e4c4a7e
Source dataset
uspto-grants-1984_01
Patent number
US04427441

Reaction notes

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