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

HRID 45989

Reaction equation

HRID 45989 reaction equation
[CH:1]1([NH:4][CH2:5][CH2:6][OH:7])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:15][O:16][C:17]1[CH:22]=[C:21]([CH3:23])[C:20]([S:24](Cl)(=[O:26])=[O:25])=[C:19]([CH3:28])[CH:18]=1>ClCCl>[CH:1]1([N:4]([CH2:5][CH2:6][OH:7])[S:24]([C:20]2[C:21]([CH3:23])=[CH:22][C:17]([O:16][CH3:15])=[CH:18][C:19]=2[CH3:28])(=[O:26])=[O:25])[CH2:3][CH2:2]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

To a cold (0° C.) solution of 2-cyclopropylamino-ethanol (8 mmol) in dichloromethane (24 ml) and triethylamine (2.5 equiv.) a solution of 4-methoxy-2,6-dimethylbenzenesulfonyl chloride (7 mmol) in dichloromethane (12 ml) was added dropwise maintaining the temperature at 0° C. After complete addition the reaction mixture was stirred at 25° C. for 90 min by which time the reaction was complete (TLC). The reaction mixture was diluted with dichloromethane (200 ml) and washed with water and finally with brine. The organic layer was dried over sodium sulfate and evaporated to dryness to obtain the pure product. Yield: 20%

Workup

  1. additionAfter complete addition the reaction mixture
  2. washwashed with water and finally with brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated to dryness
  5. customto obtain the pure product

Sources & evidence

ORD record
ord-31017654e9994e0384e8f0702a1bee12
Source dataset
uspto-grants-2013_09
Patent number
US08541573B2

Linked notes

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