2,4-dimethyl-N-(2-methylpropyl)aniline → HCID 71543491, compound

HRID 1746422Notes

Reaction equation

HRID 1746422 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH:11]([CH3:13])[CH3:12].[N:14]1[NH:15][N:16]=[N:17][C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:10][CH:11]([CH3:13])[CH3:12])[S:25]([C:22]1[CH:21]=[CH:20][C:19]([C:18]2[N:14]=[N:15][NH:16][N:17]=2)=[CH:24][CH:23]=1)(=[O:27])=[O:26]

Participants

4

Reactant 2

HCID 284223892,4-dimethyl-N-(2-methylpropyl)anilineHCID 529112714-(2H-Tetrazol-5-yl)benzene-1-sulfonyl chloride

Product 1

HCID 71543491HCID 71543491, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of (2,4-dimethylphenyl)(2-methylpropyl)amine (100 mg, 0.564 mmol) in pyridine (2 mL) was added 4-(2H-tetrazol-5-yl)benzene-1-sulfonyl chloride (138 mg, 0.564 mmol) and the mixture stirred at 20° C. for 30 minutes, then stood at room temperature, in air, for 16 hours. The crude was then purified by flash silica (Si) chromatography (using a 25-100% ethyl acetate-cyclohexane gradient) to give a colourless gum. This was further dried under a stream of nitrogen, then under vacuum for 3 hours, to give the final product, 104.87 mg. LCMS (M+1) 386, RT 1.22 mins.

Workup

  1. waitstood at room temperature, in air, for 16 hours
  2. customThe crude was then purified by flash silica (Si) chromatography (
  3. customto give a colourless gum
  4. customThis was further dried under a stream of nitrogen
  5. waitunder vacuum for 3 hours

Sources & evidence

ORD record
ord-9c21427151824da6a16bd780dac31f66
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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