Water → HCID 54430516, compound

HRID 233491Notes

Reaction equation

HRID 233491 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.[OH:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18].[OH2:21]>N1C=CC=CC=1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([N:15]([CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])[CH2:14][CH2:13][O:12][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:8])=[O:21])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 149870161-[(2-Hydroxyethyl)amino]-2-methyl-2-propanol

Product 1

HCID 54430516HCID 54430516, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Toluenesulfonyl chloride (166.1 g) was added portionwise to a stirred solution of 1-[(2-hydroxyethyl)amino]-2-methyl-2-propanol (58.0 g) in pyridine (275 ml) at 0°-10° C. The resulting solution was stirred at room temperature for 15 h and then poured into water (1 l). The mixture was extracted with dichloromethane and the organic phase was washed with hydrochloric acid (2.5M) and brine. After drying over magnesium sulfate, the solvent was removed under reduced pressure to give 1-{N-[(4-methylphenyl)sulfonyl]-N-[(4-methylphenyl)sulfonyloxyethyl]amino}-2-methyl-2-propanol (155.8 g). δ (CDCl3) 1.23 (s,6H), 2.44,2.46 (6H), 3.08 (s,2H), 3.45 (t,2H), 4.35 (t,2H) and 7.25-7.85 (m,8H).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washthe organic phase was washed with hydrochloric acid (2.5M) and brine
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0ef93d24f82a486092953910db92c95c
Source dataset
uspto-grants-1997_01
Patent number
US05593983

Reaction notes

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