Ethanol → HCID 18691314, compound

HRID 1871358Notes

Reaction equation

HRID 1871358 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH2:20][CH3:21])[C:12]1[N:17]=[C:16](Cl)[N:15]=[C:14]([CH3:19])[N:13]=1.[Cl:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C(OCC)(=O)C.C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH2:20][CH3:21])[C:12]1[N:17]=[C:16]([C:26]2[CH:25]=[CH:24][C:23]([Cl:22])=[CH:28][C:27]=2[Cl:29])[N:15]=[C:14]([CH3:19])[N:13]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 10809134HCID 10809134, compound

Product 1

HCID 18691314HCID 18691314, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Part C: A mixture of N-(2-bromo-4-isopropylphenyl)-N-ethyl-4-chloro-6-methyl-1,3,5-triazine-2-amine (370 mg), 2,4-dichlorophenylboronic acid (210 mg) tetrakis(triphenylphoshine)palladium(0) (50 mg), 1M aqueous sodium carbonate (2 mL), ethanol (0.75 mL) and benzene (6 mL) was refluxed for 10 hr.The cooled mixture was diluted with ethyl acetate and the aqueous layer was removed. The organic layer was washed with water and brine, dried, and concentrated in vacuo The crude reaction product was chromatographed on silica gel using ethyl acetate/hexanes (1:9) as eluent. The title compound was obtained as a pure colorless viscous oil (210 mg) that crystallized on standing and trituration with petroleum ether to colorless crystals (82 mg). Elemental Analysis: Calcd. for C21H21N4Cl2Br: C, 52.52: H, 4.417; N, 11.67. Found: C, 52.79; H, 4.34; N, 11.40.

Workup

  1. temperaturewas refluxed for 10 hr
  2. customthe aqueous layer was removed
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated in vacuo The crude
  6. customreaction product
  7. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-9fdd4f36cbca4b7d9b67e0b26431d583
Source dataset
uspto-grants-2000_08
Patent number
US06103737

Reaction notes

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