HCID 69522449, compound → HCID 69521468, compound

HRID 856699Notes

Reaction equation

HRID 856699 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][S:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[N:6][N:5]=[N:4]1)[CH3:2].[CH2:19]([N:21]1[N:25]=[N:24][C:23]([CH2:26][S:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=2)=[N:22]1)[CH3:20]>C(O)(=O)C>[CH2:1]([N:3]1[C:7]([CH2:8][S:9][C:10]2[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)=[N:6][N:5]=[N:4]1)[CH3:2].[CH2:19]([N:21]1[N:25]=[N:24][C:23]([CH2:26][S:27][C:28]2[CH:29]=[CH:30][C:31]([NH2:34])=[CH:32][CH:33]=2)=[N:22]1)[CH3:20]

Participants

5

Reactant 2

HCID 69522449HCID 69522449, compoundHCID 69522609HCID 69522609, compound

Product 2

HCID 69521468HCID 69521468, compoundHCID 69522077HCID 69522077, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 1-ethyl-5-[[(4-nitrophenyl)sulfanyl]methyl]-1,2,3,4-tetrazole and 2-ethyl-5-[[(4-nitrophenyl)sulfanyl]methyl]-1,2,3,4-tetrazole (4.2 g) was added acetic acid (42 ml), reduced iron (12.6 g) was added to the mixture, and the mixture was stirred for 40 hours at room temperature. The mixture was filtered with Celite, and the mixture was washed with ethyl acetate. The solvent was removed under reduced pressure, and the obtained residue was dissolved in ethyl acetate, and the mixture was washed with an aqueous solution of saturated sodium bicarbonate and saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-[[(1-ethyl-1,2,3,4-tetrazol-5-yl)methyl]sulfanyl]aniline (1.1 g) and 4-[[(2-ethyl-1,2,3,4-tetrazol-5-yl)methyl]sulfanyl]aniline (2.2 g).

Workup

  1. additionwas added to the mixture
  2. filtrationThe mixture was filtered with Celite
  3. washthe mixture was washed with ethyl acetate
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe obtained residue was dissolved in ethyl acetate
  6. washthe mixture was washed with an aqueous solution of saturated sodium bicarbonate and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7e6dc413611b430580c94bd38f691b98
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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