4-Isopropylaniline → HCID 66872646, compound

HRID 1967536Notes

Reaction equation

HRID 1967536 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.P(Cl)(Cl)Cl.C([C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1)(C)C>ClC1C=CC=CC=1>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH:31][C:30]1[CH:29]=[CH:28][C:27]([O:1][CH:2]([CH3:10])[CH3:3])=[CH:33][CH:32]=1)=[O:6]

Participants

5

Reactant 3

HCID 74644-IsopropylanilineHCID 24387Phosphorus trichlorideHCID 692994HCID 692994, compound

Product 1

HCID 66872646HCID 66872646, compoundYield 149.4%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Chlorobenzene (2.0 mL) was added to 2-hydroxy-5-(piperidin-1-ylsulfonyl)benzoic acid (470 mg), and under stirring, phosphorus trichloride (0.072 mL) was added thereto and kept stirred at 130° C. for 1 hour. 4-Isopropylaniline (249 mg) was added to it, and stirred at 130° C. for 16 hours. The solvent was evaporated off under reduced pressure, then ethyl acetate was added thereto, washed with water and saturated brine in that order, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 50%, gradient) to give the intended product (515 mg, 75%) as a colorless solid.

Workup

  1. stirringkept stirred at 130° C. for 1 hour
  2. stirringstirred at 130° C. for 16 hours
  3. customThe solvent was evaporated off under reduced pressure
  4. additionethyl acetate was added
  5. washwashed with water and saturated brine in that order
  6. dry with materialdried with sodium sulfate
  7. customThe drying agent was removed through filtration
  8. customthe solvent was evaporated off under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 50%, gradient)

Sources & evidence

ORD record
ord-afc80385380f4a3a8257d36391fd469f
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

Loading…