Hydrochloric Acid → N-phenyl 5-[2-chloro-4-(trifluoromethyl)phenoxyl]-2-nitrobenzamide

HRID 462651

Reaction equation

HRID 462651 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10](Cl)=[O:11].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl>C1(C)C=CC=CC=1>[C:26]1([NH:25][C:10](=[O:11])[C:9]2[CH:13]=[C:5]([O:4][C:3]3[CH:17]=[CH:18][C:19]([C:21]([F:24])([F:23])[F:22])=[CH:20][C:2]=3[Cl:1])[CH:6]=[CH:7][C:8]=2[N+:14]([O-:16])=[O:15])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chloride

Product 1

HCID 13475662N-phenyl 5-[2-chloro-4-(trifluoromethyl)phenoxyl]-2-nitrobenzamideYield 62.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride (5.68 g, 0.015 mole) in toluene (35 ml) was added aniline (2.8 g, 0.30 mole). The temperature immediately rose to 45° C. The reaction was then heated to reflux for twelve hours. The cooled reaction was poured into dilute hydrochloric acid solution. The residual solids were filtered, washed with warm water and dried to give 4.1 g of a gray solid m.p. 190°-4° C. Recrystallization from methanol gave 3.8 g, m.p. 191°-4° C.

Workup

  1. customimmediately rose to 45° C
  2. temperatureThe reaction was then heated
  3. temperatureto reflux for twelve hours
  4. customThe cooled reaction
  5. filtrationThe residual solids were filtered
  6. washwashed with warm water
  7. customdried

Sources & evidence

ORD record
ord-d08fa4dbf73a42c78a3b690b31957196
Source dataset
uspto-grants-1985_05
Patent number
US04517010

Linked notes

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