5-Chlorosulphonyl-2-anisic acid → HCID 71543456, compound

HRID 1746427Notes

Reaction equation

HRID 1746427 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].Cl[S:15]([C:18]1[CH:19]=[CH:20][C:21]([O:27][CH3:28])=[C:22]([CH:26]=1)[C:23]([OH:25])=[O:24])(=[O:17])=[O:16]>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:15]([C:18]1[CH:19]=[CH:20][C:21]([O:27][CH3:28])=[C:22]([CH:26]=1)[C:23]([OH:25])=[O:24])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 1040075-Chlorosulphonyl-2-anisic acidHCID 284223892,4-dimethyl-N-(2-methylpropyl)aniline

Product 1

HCID 71543456HCID 71543456, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of (2,4-dimethylphenyl)(2-methylpropyl)amine (200 mg, 1.128 mmol) in pyridine (3 mL) was added 5-(chlorosulfonyl)-2-methoxybenzoic acid (283 mg, 1.128 mmol) and the reaction stirred at 20° C. for 4 hours. The solvent was removed in vacuo and the crude purified by flash silica (Si) chromatography (using a 0-100%, ethyl acetate-dichloromethane gradient, with extra 0-20% methanol added). The appropriate fractions were combined and evaporated in vacuo to give the required product, 108 mg. LCMS (M+1) 392, RT 1.18 mins.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude purified by flash silica (Si) chromatography (
  3. additionwith extra 0-20% methanol added)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-a065f2725cca4ad6a582918614912a26
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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