4-Toluenesulfonyl chloride → HCID 23331319, compound

HRID 224564Notes

Reaction equation

HRID 224564 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH2:20][CH:21]([NH2:23])[CH3:22])[CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C>C1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH:23][CH:21]([CH3:22])[CH2:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([O:13][CH3:12])[CH:15]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1522341-(3-Methoxyphenyl)propan-2-amine

Product 1

HCID 23331319HCID 23331319, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of p-toluenesulfonyl chloride (28.0 gm., 0.15 M) in benzene (100 ml.) was added dropwise to a solution of 2-(3-methoxyphenyl)-1-methylethylamine (23 gm., 0.139 M) and triethylamine (13 gm., 0.15 M) in benzene (200 ml.) during 30 minutes. The reaction was stirred at room temperature for 4 hours. The precipitated triethylamine hydrochloride was filtered off and the benzene solution was washed with hydrochloric acid (3N), water and saturated brine. The benzene solution was dried over magnesium sulfate. Evaporation of the solvent afforded N-toluene-p-sulfonyl-2-(3-methoxyphenyl)-1-methylethylamine as an oil Wt=42 gm.

Workup

  1. filtrationThe precipitated triethylamine hydrochloride was filtered off
  2. washthe benzene solution was washed with hydrochloric acid (3N), water and saturated brine
  3. dry with materialThe benzene solution was dried over magnesium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f146a0ef8d2247ad996adfed0c77dcdb
Source dataset
uspto-grants-1980_11
Patent number
US04233217

Reaction notes

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