2,6-Difluoroaniline → HCID 178499019, compound

HRID 329575Notes

Reaction equation

HRID 329575 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[C:10]([NH:13][C:14]1[NH:18][N:17]=[C:16]([S:19](Cl)(=[O:21])=[O:20])[C:15]=1[C:23]([O:25][CH3:26])=[O:24])(=[O:12])[CH3:11]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:10]([NH:13][C:14]1[NH:18][N:17]=[C:16]([S:19]([NH:4][C:3]2[C:2]([F:1])=[CH:8][CH:7]=[CH:6][C:5]=2[F:9])(=[O:20])=[O:21])[C:15]=1[C:23]([O:25][CH3:26])=[O:24])(=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 796472,6-DifluoroanilineHCID 178499017HCID 178499017, compound

Product 1

HCID 178499019HCID 178499019, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

23.63 g (177.5 mmol) of 97% 2,6-difluoroaniline and 1.48 g N,N-dimethyl-4-aminopyridine was dissolved in 225 ml pyridine and 25.0 g (88.75 mmol) 5-acetamido-4-methoxycarbonylpyrazole-3-sulphonyl chloride added portionwise. The mixture was stirred for 48 hours at 25° C. The pyridine was distilled and the residue dissolved in 510 ml methylene chloride washed twice with 370 ml 5N hydrochloric acid and twice with 370 ml water, dried over magnesium sulphate and concentrated. The residue was triturated with ether, the product suction filtered, washed with ether and dried.

Workup

  1. distillationThe pyridine was distilled
  2. dissolutionthe residue dissolved in 510 ml methylene chloride
  3. washwashed twice with 370 ml 5N hydrochloric acid and twice with 370 ml water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue was triturated with ether
  7. filtrationthe product suction filtered
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-68db0b2e13014195b9a82c5ae80e3f37
Source dataset
uspto-grants-1990_01
Patent number
US04892576

Reaction notes

Loading…