Sodium Azide → 2-Azido-6,7-diethylnaphthalene-1,4-dione

HRID 437844Notes

Reaction equation

HRID 437844 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[C:6]1[C:7](=[O:21])[C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][C:11]([CH2:17][CH3:18])=[C:10]([CH2:19][CH3:20])[CH:9]=2>C(O)C>[N:1]([C:15]1[C:14](=[O:16])[C:13]2[C:8]([C:7](=[O:21])[CH:6]=1)=[CH:9][C:10]([CH2:19][CH3:20])=[C:11]([CH2:17][CH3:18])[CH:12]=2)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 123664012-Chloro-6,7-diethylnaphthalene-1,4-dione

Product 1

HCID 123664032-Azido-6,7-diethylnaphthalene-1,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution of sodium azide (6.15 g; 0.095 mole) was added in one portion to a stirred, refluxing solution of 2-chloro-6,7-diethyl-1,4-naphthoquinone (18.0 g; 0.073 mole) in ethanol (180 ml) and the mixture refluxed for a further 2 mins. The red solution was cooled and the orange solid filtered off and washed with cold ethanol then water. After drying the product weighed 13.87 g (75%) and had m.p. 73°-76° C. (d). Recrystallisation from ethanol gave long orange needles of m.p. 74°-76° C. (d). (Found; C, 65.64; H, 5.27; N, 16.66; C14H13N3O2 requires; C, 65.87; H, 5.13; N, 16.46%).

Workup

  1. temperaturethe mixture refluxed for a further 2 mins
  2. temperatureThe red solution was cooled
  3. filtrationthe orange solid filtered off
  4. washwashed with cold ethanol
  5. customAfter drying the product
  6. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-69174967346f4eec89c3fce7164f2334
Source dataset
uspto-grants-1977_06
Patent number
US04032544

Reaction notes

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