Benzenesulfonyl chloride → N-[2-(1-Benzyl-1H-tetrazol-5-yl)-3-methylphenyl]-benzenesulfonamide

HRID 631883Notes

Reaction equation

HRID 631883 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:20])=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([N:8]1[C:12]([C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=2[NH:20][S:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:29])=[O:28])=[N:11][N:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 613540742-(1-Benzyl-1H-tetrazol-5-yl)-3-methylphenylamine2×

Product 1

HCID 68296407N-[2-(1-Benzyl-1H-tetrazol-5-yl)-3-methylphenyl]-benzenesulfonamideYield 98.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(1-Benzyl-1H-tetrazol-5-yl)-3-methylphenylamine (Intermediate 16, 0.15 g) was dissolved in pyridine (5 mL) and benzenesulfonyl chloride (0.07 g, 0.4 mmol) was added. The mixture was stirred overnight, then diluted with ethyl acetate and washed with 1N hydrochloric acid, dried with magnesium sulfate and filtered. The filtrate was evaporated to dryness and the residue was purified by flash chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane. The fractions containing the desired product were combined and evaporated to give the title compound as a white powder (0.16 g).

Workup

  1. washwashed with 1N hydrochloric acid
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by flash chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane
  7. additionThe fractions containing the desired product
  8. customevaporated

Sources & evidence

ORD record
ord-3cd9335824854cae99e092d90fd48c34
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

Loading…