1,2,4-Trichlorobenzene → HCID 69753798, compound

HRID 1415588Notes

Reaction equation

HRID 1415588 reaction equation
Cl[C:2]1[C:3]([OH:21])=[C:4]([C:14]([OH:20])=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=1)[C:5](OC1C=CC=CC=1)=[O:6].[NH2:22]C1C=CC(C(C2C=CC(OC)=CC=2)C#N)=C(C(F)(F)F)C=1.ClC1C=CC(Cl)=CC=1Cl>>[OH:21][C:3]1[CH:2]=[CH:16][C:15]([N+:17]([O-:19])=[O:18])=[C:14]([OH:20])[C:4]=1[C:5]([NH2:22])=[O:6]

Participants

4

Reactant 3

HCID 131,2,4-TrichlorobenzeneHCID 21483104HCID 21483104, compoundHCID 21483184HCID 21483184, compound

Product 1

HCID 69753798HCID 69753798, compound

Conditions

Temperature
190 °C

Procedure

A mixture of 3 parts of phenyl 3-chloro-2,6-dihydroxy-5-nitrobenzoate, 3 parts of 4-amino-α-(4-methoxyphenyl)-2-(trifluoromethyl)benzeneacetonitrile and 30 parts of 1,2,4-trichlorobenzene is stirred for 10 minutes at 190° C. The reaction mixture is cooled and poured onto 140 parts of petroleumether while stirring. The supernatant phase is decanted and the residue is boiled in methylbenzene and stirred with activated charcoal. The latter is filtered off over hyflo. Petroleumether is added to the filtrate till turbid and the product is allowed to crystallize while stirring. It is filtered off, dried and crystallized from acetonitrile, yielding 4.5 parts of 3-chloro-N-{4-[α-cyano-α-(4-methoxyphenyl)methyl]-3-trifluoromethyl)phenyl}-2,6-dihydroxy-5-nitrobenzamide; mp. 206.4° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. additionpoured onto 140 parts of petroleumether
  3. stirringwhile stirring
  4. customThe supernatant phase is decanted
  5. stirringstirred with activated charcoal
  6. filtrationThe latter is filtered off over hyflo
  7. additionPetroleumether is added to the filtrate till turbid
  8. customto crystallize
  9. stirringwhile stirring
  10. filtrationIt is filtered off
  11. customdried
  12. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-5af04d60a18046a1a9318ce97d08beba
Source dataset
uspto-grants-1977_01
Patent number
US04005218

Reaction notes

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