Triethylamine → 3-Ethyl-2-(4,6-bis-trichloromethyl-s-triazin-2-yl-methylene)benzothiazoline

HRID 249074

Reaction equation

HRID 249074 reaction equation
C(N(CC)CC)C.[CH2:8]([N+:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12][C:11]=1[CH3:19])[CH3:9].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[Cl:31][C:32]([C:35]1[N:40]=[C:39](C(Cl)(Cl)Cl)[N:38]=[C:37]([C:45]([Cl:48])([Cl:47])[Cl:46])[N:36]=1)([Cl:34])[Cl:33]>C1(C)C=CC=CC=1>[CH2:8]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12][C:11]1=[CH:19][C:39]1[N:40]=[C:35]([C:32]([Cl:31])([Cl:34])[Cl:33])[N:36]=[C:37]([C:45]([Cl:47])([Cl:48])[Cl:46])[N:38]=1)[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 230381,3,5-Triazine, 2,4,6-tris(trichloromethyl)-HCID 84711Benzothiazolium, 3-ethyl-2-methyl-, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 571992653-Ethyl-2-(4,6-bis-trichloromethyl-s-triazin-2-yl-methylene)benzothiazoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Within a period of half an hour, 10 g (0.1 mol) of triethylamine was added dropwise to a suspension of 35 g (0.1 mol) of 3-ethyl-2-methyl-benzothiazolium-p-toluene-sulfonate and 43 g (0.1 mol) of tris-trichloromethyl-s-triazine in 300 ml of toluene. After completion of the addition the reaction mixture was stirred for half an hour, until the exothermic reaction ceased; the product which had precipitated was filtered off and dried. Compound 2 was obtained in nearly pure form in a quantity of 40 g. By evaporating the toluene in vacuo and treating the solid residue with ethanol, another 9 g of the product resulted. After recrystallization from 2-methoxy-ethanol 40 g (82%) of yellow needles of melting point 238° to 241° C. were obtained.

Workup

  1. waitWithin a period of half an hour
  2. additionAfter completion of the addition the reaction mixture
  3. customthe product which had precipitated
  4. filtrationwas filtered off
  5. customdried

Sources & evidence

ORD record
ord-5ef6a5ddbfb549e1b1f3c4cd967f388b
Source dataset
uspto-grants-1993_05
Patent number
US05212307

Linked notes

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