Cyanuric chloride → HCID 23501186, compound

HRID 1363885Notes

Reaction equation

HRID 1363885 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[N:3]=1.O1CCCC1.[NH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.C(N(CC)CC)C>O1CCOCC1>[Cl:9][C:4]1[N:5]=[C:6]([Cl:8])[N:7]=[C:2]([NH:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[N:3]=1

Participants

6

Reactant 4

HCID 7954Cyanuric chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 133964-Aminobenzonitrile

Product 1

HCID 23501186HCID 23501186, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
-75 °C

Procedure

2,4,6-trichloro-1,3,5-triazine (0.07440 mol) and tetrahydrofuran (100 ml) were combined and cooled to −75° C. under Ar atmosphere. 4-Aminobenzonitrile (0.07440 mol) was added and the solution was stirred for 4 hours at −75° C. Triethylamine (0.07440 mol) was added dropwise and the reaction mixture was allowed to warm up slowly to room temperature and stirred for 3 days. After adding 1,4-dioxane (100 ml), the resulting precipitate was collected by filtration, washed with tetrahydrofuran, and dried, yielding 12.74 g 4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzonitrile (interm. 17).

Workup

  1. temperatureto warm up slowly to room temperature
  2. stirringstirred for 3 days
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with tetrahydrofuran
  5. customdried

Sources & evidence

ORD record
ord-b12f79ba896a412c9f85a871a4d4b6d9
Source dataset
uspto-grants-2011_02
Patent number
US07887845B2

Reaction notes

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