4-[(1-methyl-1H-benzimidazol-2-yl)oxy]aniline → HCID 21563670, compound

HRID 1580680Notes

Reaction equation

HRID 1580680 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[N:11]([CH3:12])[C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[N:8]=2)=[CH:4][CH:3]=1.Cl[C:20](Cl)(Cl)[S:21]([SH-]C(=S)[S-])(=O)=O>O>[N:1]([C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[N:11]([CH3:12])[C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[N:8]=2)=[CH:17][CH:18]=1)=[C:20]=[S:21]

Participants

4

Reactant 2

HCID 215636774-[(1-methyl-1H-benzimidazol-2-yl)oxy]anilineHCID 178527682HCID 178527682, compound

Product 1

HCID 21563670HCID 21563670, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An amount of 4.8 g of 2-(4'-aminophenoxy)-1-methylbenzimidazole is stirred with 2.3 g of bis-(trichloromethane-sulphonyl-trithiocarbonate in 25 ml of water for 24 hours at room temperature. The precipitate is separated, washed with sodium bicarbonate solution, and taken up in chloroform. After drying and distillation of the chloroform solution, the residue is boiled out with cyclohexane, filtered hot, and the filtrate diluted with petroleum ether. The 2-(4'-isothiocyanophenoxy)-1-methylbenzimidazole crystallising out melts at 59° to 61°C.

Workup

  1. customThe precipitate is separated
  2. washwashed with sodium bicarbonate solution
  3. customAfter drying
  4. distillationdistillation of the chloroform solution
  5. filtrationfiltered hot
  6. additionthe filtrate diluted with petroleum ether

Sources & evidence

ORD record
ord-eb2e0efc0e714aff98e225757c10aad3
Source dataset
uspto-grants-1976_01
Patent number
US03933841

Reaction notes

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