Toluene → 2-[4-(4,6-Bis-trichloromethyl-s-triazin-2-yl) benzoylmethylene]-3-methylbenzothiazoline

HRID 345193Notes

Reaction equation

HRID 345193 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=2[N+:6]=1[CH3:7].CC1C=CC(S(O)(=O)=O)=CC=1.[Cl:23][C:24]([Cl:45])([Cl:44])[C:25]1[N:30]=[C:29]([C:31]([Cl:34])([Cl:33])[Cl:32])[N:28]=[C:27]([C:35]2[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=2)[N:26]=1.C1(C)C=CC=CC=1>C(N(CC)CC)C>[Cl:34][C:31]([Cl:32])([Cl:33])[C:29]1[N:30]=[C:25]([C:24]([Cl:45])([Cl:23])[Cl:44])[N:26]=[C:27]([C:35]2[CH:36]=[CH:37][C:38]([C:39]([CH:1]=[C:2]3[N:6]([CH3:7])[C:5]4[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=4[S:3]3)=[O:40])=[CH:42][CH:43]=2)[N:28]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14473251HCID 14473251, compoundHCID 867451362,3-Dimethyl-benzothiazolium p-toluenesulfonate

Product 1

HCID 867451372-[4-(4,6-Bis-trichloromethyl-s-triazin-2-yl) benzoylmethylene]-3-methylbenzothiazoline

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2,3-Dimethylbenzothiazolium-p-toluenesulfonate (13.4 pbw) and 4-(4,6-bis-trichloromethyl-s-triazin2-yl)-benzoylchloride (22.7 pbw) are successively suspended or dissolved, respectively, in 150 pbw of toluene. The mixture is cooled to 15° C. and with the exclusion of moisture 13.1 pbw of triethylamine are added dropwise at this temperature. The mixture discolors towards dark brown and is stirred for 3 hours at room temperature. The precipitate formed is removed by filtration with suction and washed with cold toluene. The residue is digested in 200 pbw of methanol and stirred for about 60 minutes, again filtered and dried.

Workup

  1. dissolutiondissolved
  2. additionare added dropwise at this temperature
  3. customThe precipitate formed
  4. customis removed by filtration with suction
  5. washwashed with cold toluene
  6. stirringstirred for about 60 minutes
  7. filtrationagain filtered
  8. customdried

Sources & evidence

ORD record
ord-c979926e303f4c88b1dbb09f16ae3759
Source dataset
uspto-grants-1991_10
Patent number
US05055579

Reaction notes

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