Hydrochloric Acid → HCID 178424083, compound

HRID 902099Notes

Reaction equation

HRID 902099 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[N:8])=[CH:3][CH:2]=1.[N-:10]=[N+:11]=[N-:12].[Na+].Cl>CN(C=O)C>[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:12][N:11]=[N:10][N:8]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7724p-TolunitrileHCID 33557Sodium Azide

Product 1

HCID 178424083HCID 178424083, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

A solution of 10.0 grams (0.085 mole) of para-toluonitrile in 160 mL of DMF was stirred and 5.6 grams (0.085 mole) of sodium azide was added. Upon completion of addition, the reaction mixture was warmed to 135° C. where it stirred for three hours. The reaction mixture was then cooled and poured into 200 mL of stirred, cold aqueous 1N hydrochloric acid. Upon completion of addition, the mixture was stirred for five minutes and filtered to collect a white solid. The solid was dried for 16 hours in a vacuum oven at 35-40° C., yielding 7.1 grams of the subject compound. The reaction was repeated.

Workup

  1. additionUpon completion of addition
  2. temperatureThe reaction mixture was then cooled
  3. additionpoured into 200 mL
  4. stirringof stirred
  5. additionUpon completion of addition
  6. stirringthe mixture was stirred for five minutes
  7. filtrationfiltered
  8. customto collect a white solid
  9. customThe solid was dried for 16 hours in a vacuum oven at 35-40° C.

Sources & evidence

ORD record
ord-ccff016f41fb4ac38101f37ccc433014
Source dataset
uspto-grants-2008_04
Patent number
US07365082B2

Reaction notes

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