4-Chloro-3-nitrophenyl methyl sulfone → 4-(beta,gamma-Dihydroxypropyl)amino-3-nitrophenyl methyl sulfone

HRID 2291968Notes

Reaction equation

HRID 2291968 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](Cl)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)(=[O:4])=[O:3].[NH2:15][CH2:16][CH:17]([OH:20])[CH2:18][OH:19]>CS(C)=O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:15][CH2:16][CH:17]([OH:20])[CH2:18][OH:19])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 667964-Chloro-3-nitrophenyl methyl sulfoneHCID 735613-Amino-1,2-propanediol

Product 1

HCID 212775904-(beta,gamma-Dihydroxypropyl)amino-3-nitrophenyl methyl sulfoneYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 4-chloro-3-nitrophenyl methyl sulfone (5 g, 21 mmole) and 3-amino-1,2-propanediol (4.25 g, 47 mmole) in DMSO (15 ml) was stirred at 23° C. for 30 min. and poured into crushed ice. The resulting yellow crystal was collected by filtration and washed with ice-cold water to give the compound (21) (5.2 g, 95%) (m.p. 133° C.).

Workup

  1. additionpoured
  2. custominto crushed ice
  3. filtrationThe resulting yellow crystal was collected by filtration
  4. washwashed with ice-cold water

Sources & evidence

ORD record
ord-5ce0f537163047d58f2606cb18a53e67
Source dataset
uspto-grants-1989_01
Patent number
US04799934

Reaction notes

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