Hydrochloric Acid → HCID 13015361, compound

HRID 839632Notes

Reaction equation

HRID 839632 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10](C(NN)=O)[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[N:19]([O-])=O.[Na+].C1(C2C=CN=C(C(N=[N+]=[N-])=S)C=2)C=CC=CC=1.[N-]=[N+]=[N-]>C(O)(=O)C.O>[C:1]1([S:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH2:19])[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 33558AzideHCID 130153604-(Phenylthio)-2-pyridinecarboxylic acid hydrazideHCID 23668193Sodium NitriteHCID 131711123HCID 131711123, compound

Product 1

HCID 13015361HCID 13015361, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 4-phenylthiopicolinic acid hydrazide 2.3 g. (0.050 mole) in 4.3 ml. of concentrated hydrochloric acid and 25 ml. of water is cooled to 75° C and a solution of 3.55 g. of sodium nitrite in 6 ml. of water is added. The solution is stirred at 0°-5° for 20 minutes after the addition is complete. The resultant suspension is extracted with methylene chloride and the combined extracts are dried over sodium sulfate and evaporated in vacuo to yield 12.7 gm. of crude 4-phenylthio picolinic acid azide. The azide is heated in 60 ml. of 50% aqueous acetic acid at steam bath temperature for 40 minutes. The suspension is filtered and the filtrate is made basic with 50% sodium hydroxide. The solids are collected by filtration, washed with water, dried and chromatographed on silica gel. Elution with ethyl acetate yields 4-phenylthio 2-amino pyridine, the structure of which is characterized analytically.

Workup

  1. additionafter the addition
  2. extractionThe resultant suspension is extracted with methylene chloride
  3. dry with materialthe combined extracts are dried over sodium sulfate
  4. customevaporated in vacuo
  5. customto yield 12.7 gm
  6. filtrationThe suspension is filtered
  7. filtrationThe solids are collected by filtration
  8. washwashed with water
  9. customdried
  10. customchromatographed on silica gel
  11. washElution with ethyl acetate

Sources & evidence

ORD record
ord-9136afc2c3e54efc8c74dc3b25576ebd
Source dataset
uspto-grants-1978_06
Patent number
US04096264

Reaction notes

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