2-Aminothiophenol → HCID 15875280, compound

HRID 1636973Notes

Reaction equation

HRID 1636973 reaction equation
[CH2:1]([CH:3]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:14])[CH3:2].CC1NC2C=CC=CC=2N=1.C(C(CCCC)CBr)C.[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[SH:45].[S]>N1C=CC=CC=1>[CH2:1]([CH:3]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C:14]1[S:45][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[N:38]=1)[CH3:2]

Participants

7

Reactant 5

HCID 87132-AminothiophenolHCID 119842-MethylbenzimidazoleHCID 868042-Ethylhexyl bromideHCID 5362487SulfurHCID 10911774HCID 10911774, compound

Product 1

HCID 15875280HCID 15875280, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

48.8 g (0.2 mol) of 1-(2-ethylhexyl)-2-methylbenzimidazole (prepared by the alkylation of 2-methylbenzimidazole and 2-ethylhexyl bromide under phase transfer conditions), 25 g (0.2 mol) of o-aminothiophenol and 19.2 g (0.6 mol) of sulphur in 200 ml of pyridine are heated for 18 hours under reflux. Then the pyridine is distilled off and the remaining residue is dissolved by heating in 80 g of ethanol. After cooling, 55.2 g (76% of theory) of the product, which, according to its melting point and HPLC and UV analysis, is identical to the compound obtained in Example 18 by route A, are precipitated.

Workup

  1. temperatureare heated for 18 hours
  2. temperatureunder reflux
  3. distillationThen the pyridine is distilled off
  4. dissolutionthe remaining residue is dissolved
  5. temperatureby heating in 80 g of ethanol
  6. temperatureAfter cooling
  7. customare precipitated

Sources & evidence

ORD record
ord-25bc8a56c2854f0ebea6637e25194007
Source dataset
uspto-grants-2000_03
Patent number
US06037473

Reaction notes

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