Hydrochloric Acid → HCID 21498840, compound

HRID 1730033Notes

Reaction equation

HRID 1730033 reaction equation
[NH:1]([C:3]([C:5]1[O:9][N:8]=[C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[N:6]=1)=[O:4])[NH2:2].Cl.[N:21]([O-])=O.[Na+]>C(O)(=O)C.O>[N:1]([C:3]([C:5]1[O:9][N:8]=[C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[N:6]=1)=[O:4])=[N+:2]=[N-:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21498858HCID 21498858, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21498840HCID 21498840, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

5-Hydrazinocarbonyl-3-α-naphthyl-1,2,4-oxadiazole (6.47g.) was dissolved in acetic acid (125 ml.) and 2N-hydrochloric acid (75 ml.). A solution of sodium nitrite (2.0g) in water (6 ml.) as added at 0° with stirring. After 15 minutes the precipitate was filtered off and dissolved in chloroform. The chloroform solution was washed with water and dried (MgSO4). Evaporation to dryness gave title compound (5.82 g.), m.p. 114° (decomp.), λmax. (EtOH) 300 nm. (ε 8,250), νmax. (CHBr3) 1710 (C=O), 2150 and 2190 cm.-1 (N3).

Workup

  1. filtrationAfter 15 minutes the precipitate was filtered off
  2. dissolutiondissolved in chloroform
  3. washThe chloroform solution was washed with water
  4. dry with materialdried (MgSO4)
  5. customEvaporation to dryness

Sources & evidence

ORD record
ord-0befccaf37ff4787a1c6d7615958574a
Source dataset
uspto-grants-1976_11
Patent number
US03991067

Reaction notes

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