Methanesulfonyl chloride → HCID 13674774, compound

HRID 1649998Notes

Reaction equation

HRID 1649998 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[NH:10][CH2:11][CH:12]([OH:14])[CH3:13].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>N1C=CC=CC=1>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[NH:10][CH2:11][CH:12]([O:14][S:16]([CH3:15])(=[O:18])=[O:17])[CH3:13]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 13674769HCID 13674769, compound

Product 1

HCID 13674774HCID 13674774, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5.0 g (19.5 mmoles) of 1-(2,6-dichlorophenyl-amino)-2-propanol hydrochloride are added in small portions to 50 ml of dry pyridine, and then 3.1 ml (4.6 g, 40 mmoles) of methanesulfonyl chloride are added dropwise, within 0.5 hours, to the mixture at 15° C. The mixture is stirred at room temperature for one hour, then further 0.8 ml (1.2 g, 10 mmoles) of methanesulfonyl chloride are added, and stirring is continued for one hour. The mixture is poured then onto 100 ml of ice water, and the aqueous mixture is extracted thrice with 70 ml of 1,2-dichloroethane, each. The dichloroethane solutions are combined, washed thrice with 50 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. 5.52 g (79.5%) of 1-(2,6-dichlorophenyl-amino)-2-methanesulfonyloxy-propane are obtained as a dark yellow oil; this substance can be utilized in the subsequent reaction without purification.

Workup

  1. stirringstirring
  2. waitis continued for one hour
  3. additionThe mixture is poured
  4. extractiononto 100 ml of ice water, and the aqueous mixture is extracted thrice with 70 ml of 1,2-dichloroethane
  5. washwashed thrice with 50 ml of water
  6. dry with materialeach, dried over anhydrous magnesium sulfate
  7. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-f5e02991cd804f6d85203af400aeee31
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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