Triethylamine → N-Cyclopropyl-N-(2-hydroxyethyl)-4-methoxy-2,6-dimethylphenylsulfonamide

HRID 2059884Notes

Reaction equation

HRID 2059884 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10](Cl)(=[O:12])=[O:11])=[C:5]([CH3:14])[CH:4]=1.[CH:15]1([NH:18][CH2:19][CH2:20][OH:21])[CH2:17][CH2:16]1.C(N(CC)CC)C>ClCCl>[CH:15]1([N:18]([CH2:19][CH2:20][OH:21])[S:10]([C:6]2[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH3:14])(=[O:12])=[O:11])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chlorideHCID 191005662-(Cyclopropylamino)ethan-1-ol

Product 1

HCID 43577600N-Cyclopropyl-N-(2-hydroxyethyl)-4-methoxy-2,6-dimethylphenylsulfonamideYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 4-methoxy-2,6-dimethylbenzenesulfonyl chloride (7 mmol) in dichloromethane (12 ml) was slowly added dropwise to a solution of 2-(cyclopropylamino)ethanol (8 mmol) in dichloromethane (24 ml) and triethylamine (2.5 eq), cooled to 0° C. On completion of the addition the mixture was stirred for 90 min at 25° C. until the reaction was complete. The mixture was diluted with dichloromethane (200 ml) and washed with water and saturated NaCl solution. The organic phase was dried over MgSO4, filtered and concentrated completely to obtain the desired product. Yield: 20%

Workup

  1. additionOn completion of the addition the mixture
  2. washwashed with water and saturated NaCl solution
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated completely

Sources & evidence

ORD record
ord-34cbee4094bb4a429442359c9aacafc7
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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