Potassium Iodide → HCID 57961562, compound

HRID 541884Notes

Reaction equation

HRID 541884 reaction equation
Cl.Cl.Cl.[Cl:4][C:5]1[CH:6]=[N:7][C:8]2[NH:9][C:10]3[CH:11]=[N:12][CH:13]=[C:14]([CH:27]=3)[CH2:15][CH2:16][C:17]3[CH:25]=[C:21]([NH:22][C:23]=1[N:24]=2)[CH:20]=[CH:19][C:18]=3N.N([O-])=O.[Na+].[I-:32].[K+].[Cu](C#N)C#N>S(=O)(=O)(O)O.O>[Cl:4][C:5]1[CH:6]=[N:7][C:8]2[NH:9][C:10]3[CH:11]=[N:12][CH:13]=[C:14]([CH:27]=3)[CH2:15][CH2:16][C:17]3[CH:25]=[C:21]([NH:22][C:23]=1[N:24]=2)[CH:20]=[CH:19][C:18]=3[I:32]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 66896687HCID 66896687, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 57961562HCID 57961562, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent

Procedure

To a suspension of 6-chloro-2,4,8,18,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-amine trihydrochloride (30.0 mg, 0.067 mmol) (prepared in Example B19, step F) in 2.0 M of sulfuric acid in water (0.502 mL) was added a solution of sodium nitrite (6.93 mg, 0.10 mmol) in water dropwise at 0° C. After addition, the resultant cloudy solution was stirred at same temperature for 1 h. Then this cold solution was added dropwise to a solution of potassium iodide (16.7 mg, 0.10 mmol) and copper cyanide (0.90 mg, 0.01 mmol) in water at 0° C. The resultant mixture was stirred at rt overnight. The precipite was filtered and washed by water and dried to give the desired product as a light brown powder (28 mg, 93%). LCMS for C17H14ClIN5 (M+H)+: m/z=449.9.

Workup

  1. additionAfter addition
  2. filtrationThe precipite was filtered
  3. washwashed by water
  4. customdried

Sources & evidence

ORD record
ord-a9709cadfd6b4c2ebf80d40959f785cd
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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