2,4-Dichloro-6-methoxy-3,5-triazine → HCID 20337591, compound

HRID 1863359Notes

Reaction equation

HRID 1863359 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([Cl:9])[N:6]=[C:5](Cl)[N:4]=1.C([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=C.[CH:20](N(CC)C(C)C)(C)[CH3:21]>CC(C)=O>[CH3:1][O:2][C:3]1[N:4]=[C:5]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([CH:20]=[CH2:21])=[CH:18][CH:19]=2)[N:6]=[C:7]([Cl:9])[N:8]=1

Participants

5

Reactant 3

HCID 192672,4-Dichloro-6-methoxy-3,5-triazineHCID 81531DiisopropylethylamineHCID 6852359N-ethenylaniline

Product 1

HCID 20337591HCID 20337591, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 16.4 g. (0.1 mole) 2-methoxy-4,6-dichloro-s-triazine in 150 ml. of acetone being stirred at 0°-5° C. was added dropwise over a 1/2 hr. period a solution of 11.9 g. (0.1 mole) of vinylaniline and 12.9 g. (0.1 mole) of N,N-di-iso-propylethylamine. After stirring at room temperature for 2 hr., the solution was poured into 1 l of ice water to isolate the product. The crude product was collected by filtration and dried in vacuo at room temperature to give 24.9 g. Recrystallization was effected by dissolution in 75 ml. of hot benzene followed by addition of ligroin to the cloud point. Yield=20.5 g. (78%) (mp 118°-122°).

Workup

  1. additionwas added dropwise over a 1/2 hr
  2. customto isolate the product
  3. filtrationThe crude product was collected by filtration
  4. customdried in vacuo at room temperature
  5. customto give 24.9 g
  6. customRecrystallization
  7. dissolutionwas effected by dissolution in 75 ml
  8. additionof hot benzene followed by addition of ligroin to the cloud point

Sources & evidence

ORD record
ord-b8834865a70347879c7dca3b1753dcf7
Source dataset
uspto-grants-1979_09
Patent number
US04168976

Reaction notes

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