HCID 69521177, compound → HCID 69522534, compound

HRID 856690Notes

Reaction equation

HRID 856690 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][S:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)=[N:5][N:4]=[N:3]1.[CH3:18][N:19]1[N:23]=[N:22][C:21]([CH2:24][S:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=2)=[N:20]1>C(O)(=O)C>[CH3:1][N:2]1[C:6]([CH2:7][S:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[N:5][N:4]=[N:3]1.[CH3:18][N:19]1[N:23]=[N:22][C:21]([CH2:24][S:25][C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)=[N:20]1

Participants

5

Reactant 2

HCID 69521177HCID 69521177, compoundHCID 69522097HCID 69522097, compound

Product 2

HCID 69522534HCID 69522534, compoundHCID 69523031HCID 69523031, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 1-methyl-5-[[(4-nitrophenyl)sulfanyl]methyl]-1,2,3,4-tetrazole and 2-methyl-5-[[(4-nitrophenyl)sulfanyl]methyl]-1,2,3,4-tetrazole (6.3 g, 1:1) were added acetic acid (63 ml) and then, reduced iron (18.9 g), and the mixture was stirred for 18 hours at room temperature. The mixture was filtered with Celite, and washed with ethyl acetate. The solvent was removed under reduced pressure, and the obtained residue was dissolved in ethyl acetate. The organic layer 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-methyl-1,2,3,4-tetrazol-5-yl)methyl]sulfanyl]aniline (1.7 g) and 4-[[(2-methyl-1,2,3,4-tetrazol-5-yl)methyl]sulfanyl]aniline (1.6 g).

Workup

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

Sources & evidence

ORD record
ord-4c9f157ee07d4f439ff32c7275236b32
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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