4-Toluenesulfonyl chloride → HCID 23331319, compound

HRID 2057480Notes

Reaction equation

HRID 2057480 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 (28.8 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 (3 N), 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 (3 N), 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-17c2467389794127bd40d6c69143e9d1
Source dataset
uspto-grants-1980_07
Patent number
US04210749

Reaction notes

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