Water → 2-[4-(4,6-Bis-trichloromethyl-s-triazin-2-yl)benzoylmethylene]-1-methyl-1,2-dihydroquinoline

HRID 345198Notes

Reaction equation

HRID 345198 reaction equation
C(N(CC)CC)C.[CH3:8][N+:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[CH3:19].CC1C=CC(S(O)(=O)=O)=CC=1.[Cl:31][C:32]([Cl:53])([Cl:52])[C:33]1[N:38]=[C:37]([C:39]([Cl:42])([Cl:41])[Cl:40])[N:36]=[C:35]([C:43]2[CH:51]=[CH:50][C:46]([C:47](Cl)=[O:48])=[CH:45][CH:44]=2)[N:34]=1.O>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:42][C:39]([Cl:40])([Cl:41])[C:37]1[N:38]=[C:33]([C:32]([Cl:53])([Cl:31])[Cl:52])[N:34]=[C:35]([C:43]2[CH:44]=[CH:45][C:46]([C:47]([CH:19]=[C:10]3[CH:11]=[CH:12][C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:9]3[CH3:8])=[O:48])=[CH:50][CH:51]=2)[N:36]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 14473251HCID 14473251, compoundHCID 86745141HCID 86745141, compound

Product 1

HCID 867451422-[4-(4,6-Bis-trichloromethyl-s-triazin-2-yl)benzoylmethylene]-1-methyl-1,2-dihydroquinoline

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (17.4 pbw) are added dropwise at 15° C. to 14.1 pbw of 1,2-dimethyl-quinolinium-p-toluenesulfonate and 22.2 pbw of 4-(4,6-bis-trichloromethyl-s-triazin-2-yl)-benzoylchloride in 150 ml of dried toluene. The mixture is then allowed to warm to room temperature. After 1 hour the mixture is poured onto 600 pbw of water, admixed with 600 pbw of methylene chloride and extracted by shaking. Silica gel (100 pbw) is added to the dried organic phase and the mixture is stirred for 30 minutes. The silica gel is removed by filtration and the solvents are distilled off in vacuo the residue is recrystallized from 2-methoxyethanol, giving strong red crystals.

Workup

  1. extractionextracted
  2. additionSilica gel (100 pbw) is added to the dried organic phase
  3. stirringthe mixture is stirred for 30 minutes
  4. customThe silica gel is removed by filtration
  5. distillationthe solvents are distilled off in vacuo the residue
  6. customis recrystallized from 2-methoxyethanol
  7. customgiving strong red crystals

Sources & evidence

ORD record
ord-8f45e78cd8554e72a11eefbbd6c96278
Source dataset
uspto-grants-1991_10
Patent number
US05055579

Reaction notes

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