Allylamine → HCID 12881155, compound

HRID 1902590Notes

Reaction equation

HRID 1902590 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][C:5](OC2C=CC=CC=2)=[C:4]([N+:22]([O-:24])=[O:23])[CH:3]=1.[CH2:25]([NH2:28])[CH:26]=[CH2:27]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N+:22]([O-:24])=[O:23])[C:5]([NH:28][CH2:25][CH:26]=[CH2:27])=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 7853AllylamineHCID 20514529HCID 20514529, compound

Product 1

HCID 12881155HCID 12881155, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 63.3 gm of 6-chloro-4-nitro-1,3-diphenoxy-benzene, 120 ml of dioxane and allylamine in substantial excess over the stoichiometrically required amount was heated for 12 hours at 60° C. Thereafter, the dioxane was distilled off, the residue was dissolved in methylene chloride, the resulting solution was washed with dilute sodium hydroxide, the organic phase was dried with sodium sulfate, and the methylene chloride was distilled off. The residue was recrystallized from a mixture of toluene and hexane and further purified on a silicagel column, yielding 51 gm (83.6% of theory) of the title compound, m.p. 81°-82° C.

Workup

  1. distillationThereafter, the dioxane was distilled off
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washthe resulting solution was washed with dilute sodium hydroxide
  4. dry with materialthe organic phase was dried with sodium sulfate
  5. distillationthe methylene chloride was distilled off
  6. customThe residue was recrystallized from a mixture of toluene and hexane
  7. customfurther purified on a silicagel column

Sources & evidence

ORD record
ord-9d11a70e2ce44c99afbd57c55448037d
Source dataset
uspto-grants-1982_12
Patent number
US04364875

Reaction notes

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