Hydrogen Sulfide → 1-(2,4-Difluorophenyl)-1-(6-thiocarbamoylbenzothiazol-2-yl)-2-(1H-1,2,4-triazol-yl)ethanol

HRID 482067Notes

Reaction equation

HRID 482067 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:17]1[S:18][C:19]2[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:20]=2[N:21]=1)([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C(N(CC)CC)C.[SH2:35].O>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:17]1[S:18][C:19]2[CH:25]=[C:24]([C:26](=[S:35])[NH2:27])[CH:23]=[CH:22][C:20]=2[N:21]=1)([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

7

Reactant 4

HCID 402Hydrogen SulfideHCID 962WaterHCID 8471TriethylamineHCID 107861891-(2,4-Difluorophenyl)-1-(6-cyanobenzothiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol

Product 1

HCID 99317771-(2,4-Difluorophenyl)-1-(6-thiocarbamoylbenzothiazol-2-yl)-2-(1H-1,2,4-triazol-yl)ethanol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(2,4-Difluorophenyl)-1-(6-cyanobenzothiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol (418 mg) and triethylamine (500 ml) were dissolved in dimethylformamide (4 ml). While chilling with ice water, hydrogen sulfide gas was introduced into the resultant solution for 5 minutes. After left over for 6 hours at room temperature, water and ethyl acetate were added to the solution to separate liquid layers. An organic layer was washed twice with water and then with saline and then dried over magnesium sulfate. The solvent was distilled out to obtain the intended compound (437 mg). Its physical properties are shown in Table 2 which will be described subsequently.

Workup

  1. customto separate liquid layers
  2. washAn organic layer was washed twice with water
  3. dry with materialwith saline and then dried over magnesium sulfate
  4. distillationThe solvent was distilled out

Sources & evidence

ORD record
ord-ad747f6fb73440dd8ea16546aeb3dec2
Source dataset
uspto-grants-1998_08
Patent number
US05792781

Reaction notes

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