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

HRID 345196Notes

Reaction equation

HRID 345196 reaction equation
[CH2:1]([N+:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]=1[CH3:12])[CH3:2].CC1C=CC(S(O)(=O)=O)=CC=1.[Cl:24][C:25]([Cl:46])([Cl:45])[C:26]1[N:31]=[C:30]([C:32]([Cl:35])([Cl:34])[Cl:33])[N:29]=[C:28]([C:36]2[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=2)[C:39](Cl)=[O:40])[N:27]=1.C1(C)C=CC=CC=1>C(N(CC)CC)C>[Cl:35][C:32]([Cl:33])([Cl:34])[C:30]1[N:31]=[C:26]([C:25]([Cl:46])([Cl:24])[Cl:45])[N:27]=[C:28]([C:36]2[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=2)[C:39]([CH:12]=[C:4]2[N:3]([CH2:1][CH3:2])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[S:5]2)=[O:40])[N:29]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 145729223-(4,6-Bis-trichloromethyl-s-triazin-2-yl) benzoylchlorideHCID 867451383-Ethyl-2-methyl-1,3-benzothiazol-3-ium;4-methylbenzenesulfonic acid

Product 1

HCID 867451402-[3-(4,6-Bis-trichloromethyl-s-triazin-2-yl)benzoylmethylene]-3-ethyl-benzothiazoline

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

3-Ethyl-2-methyl-benzothiazolium-p-toluenesulfonate (5.0 pbw) and 3-(4,6-bis-trichloromethyl-s-triazin-2-yl) benzoylchloride (7.4 pbw) are successively suspended or dissolved, respectively, in 50 pbw of toluene. The mixture is cooled to 15° C. and, at this temperature, 6.0 pbw of triethylamine are added dropwise with the exclusion of moisture. The mixture discolors towards dark brown and is stirred for 3 hours at room temperature. The precipitate that forms 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, filtered again and dried. The product is recrystallized from 2-methoxy-ethanol, giving orange-colored crystals.

Workup

  1. dissolutiondissolved
  2. additionare added dropwise with the exclusion of moisture
  3. customThe precipitate that forms is removed by filtration with suction
  4. washwashed with cold toluene
  5. stirringstirred for about 60 minutes
  6. filtrationfiltered again
  7. customdried
  8. customThe product is recrystallized from 2-methoxy-ethanol
  9. customgiving orange-colored crystals

Sources & evidence

ORD record
ord-844d56ae32684c6a9fc1bb4de4f0426f
Source dataset
uspto-grants-1991_10
Patent number
US05055579

Reaction notes

Loading…