3-Chloroaniline → HCID 67389233, compound

HRID 913281Notes

Reaction equation

HRID 913281 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10](Cl)[N:9]=2)[N:5]=[CH:4][N:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].[CH3:23][O:24][CH2:25][CH:26]([NH2:28])[CH3:27]>O1CCCC1>[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][N:11]=[C:10]([NH:28][CH:26]([CH3:27])[CH2:25][O:24][CH3:23])[N:9]=3)[N:5]=[CH:4][N:3]=2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 79323-ChloroanilineHCID 123458MethoxyisopropylamineHCID 86646773HCID 86646773, compound2×

Product 1

HCID 67389233HCID 67389233, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-4-(2-chloro-4-pyrimidinyl)-1,3,5-triazine (i.e., the product of Step B) (25 mg, 0.11 mmol) in tetrahydrofuran (1.0 mL) was added 3-chloroaniline (0.1 mL). The resulting mixture was stirred at room temperature for 3 h to generate a yellow suspension. To this suspension was added 1-methoxy-2-propylamine (0.2 mL), and the resulting mixture was refluxed for 5 h. The solution was concentrated and purified using column chromatography on silica gel eluted with 70% ethyl acetate in hexanes to give 30 mg of the title compound as a yellow solid.

Workup

  1. temperaturethe resulting mixture was refluxed for 5 h
  2. concentrationThe solution was concentrated
  3. custompurified
  4. washeluted with 70% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-60a98d8694aa4b519ef08a5af8aca787
Source dataset
uspto-grants-2011_09
Patent number
US08026359B2

Reaction notes

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