Dichloromethane → HCID 17789755, compound

HRID 1266195Notes

Reaction equation

HRID 1266195 reaction equation
ClN1C(=O)CCC1=O.Cl[CH2:10][Cl:11].[CH2:12]([N:14]1[C:19](=[O:20])C=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]=[C:15]1[NH:25][C:26]1[C:31]([F:32])=[C:30]([F:33])[C:29]([F:34])=[C:28]([F:35])[C:27]=1[F:36])[CH3:13].[Cl-].[NH4+]>CCOCC>[Cl:11][C:10]1[C:19](=[O:20])[N:14]([CH2:12][CH3:13])[C:15]([NH:25][C:26]2[C:27]([F:36])=[C:28]([F:35])[C:29]([F:34])=[C:30]([F:33])[C:31]=2[F:32])=[N:16][C:17]=1[C:21]([F:22])([F:24])[F:23]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 31398ChlorosuccinimideHCID 18549222HCID 18549222, compound

Product 1

HCID 17789755HCID 17789755, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-Chlorosuccinimide (0.61 g, 5.15 mmol) was added at room temperature to dichloromethane (15 ml) solution of 3-ethyl-2-(2,3,4,5,6-pentafluorophenyl)amino-6-trifluoromethyl-4(3H)-pyrimidinone (1.28 g, 3.42 mmol), followed by stirring at the same temperature for 24 hours. After completion of the reaction, ether (20 ml) and saturated ammonium chloride aqueous solution (10 ml) were added to the reaction solution to separate the organic layer, and the aqueous layer was extracted with ether (10 ml×2). The organic layers were combined, washed with saturated brine and then dried over anhydrous sodium sulfate. The drying agent was removed by filtration, and the resulting filtrate was concentrated under a reduced pressure. By purifying the thus obtained crude product by a silica gel column chromatography (hexane:ethyl acetate=3:1˜1:1), white solid of 5-chloro-3-ethyl-2-(2,3,4,5,6-pentafluorophenyl) amino-6-trifluoromethyl-4 (3H)-pyrimidinone [Compound No. 17] was obtained.

Workup

  1. additionwere added to the reaction solution
  2. customto separate the organic layer
  3. extractionthe aqueous layer was extracted with ether (10 ml×2)
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe drying agent was removed by filtration
  7. concentrationthe resulting filtrate was concentrated under a reduced pressure
  8. customBy purifying the

Sources & evidence

ORD record
ord-f366f6041e7f4a68810ca7d56d3d15d9
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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