Hydrochloric Acid → HCID 15057639, compound

HRID 654028Notes

Reaction equation

HRID 654028 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].N1C=CC=CC=1.[CH3:17][O:18][C:19](=[O:34])[C:20]1[CH:29]=[C:28]([S:30](Cl)(=[O:32])=[O:31])[CH:27]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=1.Cl>ClC(Cl)C>[CH3:17][O:18][C:19](=[O:34])[C:20]1[CH:29]=[C:28]([S:30](=[O:31])(=[O:32])[NH:4][C:3]2[C:2]([F:1])=[CH:8][C:7]([F:9])=[CH:6][C:5]=2[F:10])[CH:27]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 677652,4,6-TrifluoroanilineHCID 37891971,3-Benzenedicarboxylic acid, 5-(chlorosulfonyl)-, 1,3-dimethyl ester

Product 1

HCID 15057639HCID 15057639, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2.94 g (20 mmol) of 2,4,6-trifluoroaniline is dissolved in 50 ml of dichloroethane with exclusion of moisture, 3.16 g (40 mmol) of pyridine is added and the solution is cooled to 0° C. With this temperature being maintained, a solution of 5.85 g (20 mmol) of 5-chlorosulfonylisophthalic acid dimethyl ester in 50 ml of dichloroethane is instilled. It is stirred for 30 more minutes at 0° C. and 5 more hours at room temperature. The suspension is shaken out three times with 2N hydrochloric acid and twice with water, the organic phase is dried on sodium sulfate, filtered, concentrated by evaporation and the residue is chromatographed on silica gel 60 (Merck) with ethyl acetate/hexane. The fractions, concentrated by evaporation, of corresponding polarity yield 6.34 g (15.72 mmol)=78.6% of the theoretical yield is obtained as a partially crystalline product.

Workup

  1. additionis added
  2. temperatureWith this temperature being maintained
  3. customat room temperature
  4. dry with materialtwice with water, the organic phase is dried on sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customthe residue is chromatographed on silica gel 60 (Merck) with ethyl acetate/hexane
  8. concentrationThe fractions, concentrated by evaporation, of corresponding polarity yield 6.34 g (15.72 mmol)=78.6% of the
  9. customtheoretical yield
  10. customis obtained as a partially crystalline product

Sources & evidence

ORD record
ord-e3b76afb06ad46bfbac9ca6dda53b081
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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