Hydrochloric Acid → HCID 20326489, compound

HRID 372726Notes

Reaction equation

HRID 372726 reaction equation
N[C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[N:12][C:11]([NH:14][NH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][C:9]=2[CH3:21])[CH:5]=[CH:6][CH:7]=1.Cl.N([O-])=O.[Na+].[C-:27]#[N:28].[K+]>C1(C)C=CC=CC=1.O>[C:27]([C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[N:12][C:11]([NH:14][NH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][C:9]=2[CH3:21])[CH:5]=[CH:6][CH:7]=1)#[N:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 20326491HCID 20326491, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20326489HCID 20326489, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1140TolueneSolvent

Procedure

A solution of 2.87 g. of ethyl 3-[6-(m-aminophenyl)-5-methyl-3-pyridazinyl]carbazate, 80 ml. of water, 10 ml. of concentrated hydrochloric acid is stirred at 0° and a solution of 0.76 g. of sodium nitrite in 10 ml. of water added dropwise over 10 minutes. After stirring for 15 minutes, the cold solution is added dropwise to a cold solution of 2.5 g. of cuprous cyanide, 2.27 g. of potassium cyanide, 50 ml. of water and 35 ml. of toluene. After stirring at 0° for 1 hour and at room temperature overnight, the mixture is filtered and the solid washed with water to give 4.3 g. of gray crystals. Purification gives product as crystals, m.p. 189°-190° C.

Workup

  1. additionthe cold solution is added dropwise to a cold solution of 2.5 g
  2. stirringAfter stirring at 0° for 1 hour and at room temperature overnight
  3. filtrationthe mixture is filtered
  4. washthe solid washed with water
  5. customto give 4.3 g
  6. customPurification
  7. customgives product as crystals, m.p. 189°-190° C.

Sources & evidence

ORD record
ord-48816da07cd946f7a8460be01bb36134
Source dataset
uspto-grants-1978_05
Patent number
US04092311

Reaction notes

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