4-Chloroaniline → HCID 11725783, compound

HRID 1896680Notes

Reaction equation

HRID 1896680 reaction equation
C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:34]1[CH:39]=[CH:38][C:37]([CH2:40][S:41][C:42]2[C:47]([C:48]([OH:50])=O)=[CH:46][CH:45]=[CH:44][N:43]=2)=[CH:36][CH:35]=1.[Cl:51][C:52]1[CH:58]=[CH:57][C:55]([NH2:56])=[CH:54][CH:53]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:51][C:52]1[CH:58]=[CH:57][C:55]([NH:56][C:48]([C:47]2[C:42]([S:41][CH2:40][C:37]3[CH:36]=[CH:35][N:34]=[CH:39][CH:38]=3)=[N:43][CH:44]=[CH:45][CH:46]=2)=[O:50])=[CH:54][CH:53]=1

Participants

7

Reactant 5

HCID 78124-ChloroanilineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16785671HCID 16785671, compound

Product 1

HCID 11725783HCID 11725783, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (1.6 mL, 8.9 mmol) and o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.6 g, 4.3 mmol) were added to a solution of 2-(4-pyridylmethylthio)pyridine-3-carboxylic acid (1.0 g, 4.1 mmol, Reference compound No. 1-1) and 4-chloroaniline (0.54 g, 4.3 mmol) in N,N-dimethylformamide (20 mL), then the mixture was stirred for 3 hours. A saturated aqueous sodium hydrogencarbonate solution (150 mL) was added to the reaction mixture, then the whole was extracted with ethyl acetate (150 mL). The ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution (150 mL) twice and saturated brine (150 mL) twice, and was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The precipitated solid was filtered off, was washed with diethyl ether:ethyl acetate (10:1), and was dried under reduced pressure to give 1.3 g of the target compound as a white solid. (Yield 91%)

Workup

  1. extractionthe whole was extracted with ethyl acetate (150 mL)
  2. washThe ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution (150 mL) twice
  3. dry with materialsaturated brine (150 mL) twice, and was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. filtrationThe precipitated solid was filtered off
  6. washwas washed with diethyl ether:ethyl acetate (10:1)
  7. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-d16e6866839d45469961e72fbfdb1155
Source dataset
uspto-grants-2013_08
Patent number
US08518973B2

Reaction notes

Loading…