Dimethyl Sulfoxide → HCID 17977876, compound

HRID 1733799Notes

Reaction equation

HRID 1733799 reaction equation
[OH:1][C:2]([C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:9][CH:8]=1)=[O:6])([CH3:4])[CH3:3].[N-:27]=[N+:28]=[N-:29].[Na+].CS(C)=O.O>C(OC)(C)(C)C.CCOCC>[OH:1][C:2]([C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:27]=[N+:28]=[N-:29])=[CH:9][CH:8]=1)=[O:6])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 33557Sodium AzideHCID 17977881HCID 17977881, compound

Product 1

HCID 17977876HCID 17977876, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

37.8 g. (0.1 mol) of 4-(2-p-tolylsulfonyloxyethoxy)-phenyl 2-hydroxy-2-propyl ketone (obtained by reacting compound IIa with p-toluenesulfonyl chloride) and 9.8 g. (0.15 mol) of sodium azide are stirred for one hour in 100 ml. of DMSO at 60° C. Through extractive work-up using water and ether or methyl t-butyl ether, 22.4 g. of compound IIf are obtained as a pale yellow, readily mobile oil. IR: v=2114 cm. -1 (N3).

Workup

  1. customat 60° C
  2. customof compound IIf are obtained as a pale yellow, readily mobile oil

Sources & evidence

ORD record
ord-668d79172c874118ba819bf9c7b190ee
Source dataset
uspto-grants-1996_07
Patent number
US05532112

Reaction notes

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