4-Chloroaniline → HCID 58065298, compound

HRID 1942959Notes

Reaction equation

HRID 1942959 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])[N:3]=1.CCN(C(C)C)C(C)C.[Cl:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1.C(=O)(O)[O-].[Na+]>C1COCC1.ClCCl.C(OCC)(=O)C>[Cl:8][C:6]1[N:5]=[C:4]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])[N:3]=[C:2]([NH:31][C:30]2[CH:32]=[CH:33][C:27]([Cl:26])=[CH:28][CH:29]=2)[N:7]=1

Participants

8

Reactant 4

HCID 78124-ChloroanilineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 58065263HCID 58065263, compound

Product 1

HCID 58065298HCID 58065298, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 262 mg (1 mmol) of (2,4-dicholoro-6-(2,6-difluorophenyl)-1,3,5-triazine (XXV) in 3 mL of dry THF was added at room temperature 129 mg (1 mmol) of iPr2NEt (Hunig's base) in 0.5 mL of dry THF. To this was added dropwise a solution of 127 mg (1 mmol) of 4-chloroaniline in 1.5 mL of dry THF. The reaction was stirred for 12 hr at room temperature and poured into a mixture of ethyl acetate and saturated aqueous sodium bicarbonate. The layers were separated. The aqueous layer was extracted twice with additional ethyl acetate and the combined organic layers were dried over magnesium sulfate. Filtration and evaporation provided a viscous film. The material was redissolved in dichloromethane and loaded onto a small plug of silica gel in a filter funnel. The silica gel was eluted with 10% ethyl acetate in hexanes and then 20% ethyl acetate in hexanes to afford 140 mg of the desired product (XXVI). ESI/MS 353.0, 354.9, 356.9 (M+H), 351.0, 353.0, 355.0 (M−H).

Workup

  1. customThe layers were separated
  2. extractionThe aqueous layer was extracted twice with additional ethyl acetate
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. filtrationFiltration and evaporation
  5. customprovided a viscous film
  6. customloaded onto a small plug of silica gel in a filter funnel
  7. washThe silica gel was eluted with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-df0e5fb5551f451ea178bc0b99bb71a8
Source dataset
uspto-grants-2013_03
Patent number
US08389718B2

Reaction notes

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