Triethylamine → N-[3-(Chloromethyl)phenyl]methanesulfonamide

HRID 714469Notes

Reaction equation

HRID 714469 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>O1CCCC1>[Cl:2][CH2:3][C:4]1[CH:5]=[C:6]([NH:7][S:19]([CH3:18])(=[O:21])=[O:20])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66630476145883-50-7

Product 1

HCID 11053164N-[3-(Chloromethyl)phenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

873 mg (4.903 mmol) of 3-(chloromethyl)aniline hydrochloride (Example 89A) were initially charged in 4 ml of tetrahydrofuran, and 2.48 g (24.514 mmol) of triethylamine were added. A solution of 421 mg (3.677 mmol) of methanesulfonyl chloride in 3 ml of tetrahydrofuran was slowly added dropwise, and the reaction solution was stirred at RT for 2 h. The reaction solution was concentrated using a rotary evaporator and the residue was purified by preparative HPLC (Chromasil, water/acetonitrile).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customa rotary evaporator
  3. customthe residue was purified by preparative HPLC (Chromasil, water/acetonitrile)

Sources & evidence

ORD record
ord-95cd73e7c58a42cd92ad829c8a3f6e79
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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