3,4-Dichloroaniline → HCID 11854633, compound

HRID 550355Notes

Reaction equation

HRID 550355 reaction equation
[Br:1][C:2]1[C:3]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5](O)=[O:6].O=S(Cl)Cl.[Cl:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][C:32]=1[Cl:33])[NH2:29]>C1(C)C=CC=CC=1.CC(C)=O.O>[Br:1][C:2]1[C:3]([N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)=[C:4]([CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1)[C:5]([NH:29][C:28]1[CH:30]=[CH:31][C:32]([Cl:33])=[C:26]([Cl:25])[CH:27]=1)=[O:6]

Participants

7

Reactant 3

HCID 72573,4-DichloroanilineHCID 24386Thionyl ChlorideHCID 67199911HCID 67199911, compound

Product 1

HCID 11854633HCID 11854633, compoundYield 85.6%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 3-bromo-2-piperid-1-yl-5-trifluoromethylbenzoic acid (680 mg; 1 eq.) in toluene (15 ml) is added SOCl2 (0.55 ml). After refluxing for 2 hours, the reaction medium is evaporated to dryness and the oil obtained is taken up in acetone (5 ml). This solution is added dropwise, while maintaining the temperature between 15 and 20° C., to a solution of 3,4-dichloroaniline (625 mg; 2 eq.) in water (7 ml) and acetone (10 ml). After stirring for 1 hour at room temperature, the precipitate is filtered off by suction, washed with water and dried. 820 mg of 3-bromo-N-(3,4-dichlorophenyl)-2-piperid-1-yl-5-trifluoromethylbenzamide are obtained in the form of a white solid.

Workup

  1. temperatureAfter refluxing for 2 hours
  2. customthe reaction medium is evaporated to dryness
  3. customthe oil obtained
  4. additionThis solution is added dropwise
  5. temperaturewhile maintaining the temperature between 15 and 20° C.
  6. filtrationthe precipitate is filtered off by suction
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-3e00873b665d47a4959076cc3b1d29ff
Source dataset
uspto-grants-2011_05
Patent number
US07947675B2

Reaction notes

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