Aniline → HCID 19800523, compound

HRID 1647034Notes

Reaction equation

HRID 1647034 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:14][C:15]([OH:17])=O.S(Cl)(Cl)=O.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)(Cl)Cl>[C:23]1([NH:22][C:15](=[O:17])[CH2:14][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=3)[S:6][C:2]=2[Br:1])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 24386Thionyl ChlorideHCID 19800524HCID 19800524, compound

Product 1

HCID 19800523HCID 19800523, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 5-bromo-2-(4-chlorophenyl)thiazol-4-yl-acetic acid (1 g, 3 mmol), thionyl chloride (2 equiv., 0.72 g, 6 mmol), and chloroform were heated under reflux for 2.5 hours. The reaction mixture was cooled and concentrated under reduced pressure. The residue was dissolved in CHCl3 (dry), followed by dropwise addition of aniline (2 equiv., 0.56 g, 6 mmol) and the resulting mixture refluxed for a further 5 hours. The reaction mixture cooled to room temperature and the precipitate was collected by filtration. The filtrate was concentrated under reduced pressure. The residue was triturated with EtOAc, and filtered to yield the desired product (0.4 g, 32%).

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 2.5 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in CHCl3 (dry)
  6. temperaturethe resulting mixture refluxed for a further 5 hours
  7. filtrationthe precipitate was collected by filtration
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe residue was triturated with EtOAc
  10. filtrationfiltered

Sources & evidence

ORD record
ord-75b453f066c64f96824b5edb37c208f1
Source dataset
uspto-grants-1993_01
Patent number
US05182402

Reaction notes

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