Acetone → HCID 21329302, compound

HRID 614349Notes

Reaction equation

HRID 614349 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[NH:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:21][O:22][C:16]=4[CH:15]=3)[C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2].[CH3:23][C:24]([CH3:26])=O.[OH-].[K+].C(Br)C=C>O>[N+:1]([C:4]1[CH:5]=[C:6]2[N:12]([CH2:26][CH:24]=[CH2:23])[C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:21][O:22][C:16]=4[CH:15]=3)[C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 21329297HCID 21329297, compound

Product 1

HCID 21329302HCID 21329302, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1.1 g. (0.0036 mole) of the nitro product of Step C in 175 ml. of refluxing acetone, was added 400 mg. (0.0068 mole) of powdered potassium hydroxide. The mixture was stirred and heated for 15 minutes, 1 ml. of allyl bromide was added and reflux was continued for 1.5 hours. About 50 ml. of water was then added and the resulting solution was concentrated to about 75 ml. The product, 1.2 g. crystallized and melted at 152°-153° C.

Workup

  1. additionTo a mixture of 1.1 g
  2. temperatureheated for 15 minutes
  3. temperaturereflux
  4. concentrationthe resulting solution was concentrated to about 75 ml
  5. customcrystallized

Sources & evidence

ORD record
ord-d88b08bb8727443993e13ad144289a05
Source dataset
uspto-grants-1979_03
Patent number
US04144341

Reaction notes

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