Triphosgene → HCID 59716808, compound

HRID 2224284Notes

Reaction equation

HRID 2224284 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[Cl:13][C:14]1[C:19]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)=[CH:18][N:17]=[N:16][C:15]=1[NH:27][NH2:28].ClC1N=NC=C(C2C=CC(C)=CC=2)C=1NN>C1COCC1>[Cl:13][C:14]1[C:15]2[N:16]([C:2](=[O:4])[NH:28][N:27]=2)[N:17]=[CH:18][C:19]=1[C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 94429TriphosgeneHCID 59716608HCID 59716608, compoundHCID 86599008HCID 86599008, compound

Product 1

HCID 59716808HCID 59716808, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirring solution of triphosgene (19.0 g, 64.0 mmol) in THF (200 mL) was cooled to 0° C. under argon and the mixture of 1-(4-chloro-5-p-tolylpyridazin-3-yl)hydrazine and 1-(3-chloro-5-p-tolylpyridazin-4-yl)hydrazine (3.0 g gross), prepared as described in Example 362C, was added over 3 min. The reaction mixture was allowed to warm to RT gradually and then stirred for 16 h. Solvent was removed under vacuum to reduce the reaction mixture to half its original volume, and the resulting suspension was cooled to an ice bath. Ice water (300 mL) was added, followed by stirring for 1 h. The product was collected by filtration and washed with 0.1 M aqueous HCl (50 mL×2), then H2O (50 mL×2). After drying under vacuum at 50° C. for 2 d, the title compound, 8-chloro-7-p-tolyl-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (2.2 g) was obtained as a yellow solid. MS [M+H]+ 261; HPLC retention time=2.75 min; 1HNMR (400 MHz, THF-d8) δ 11.69 (s, 1H), 8.10 (s, 1H), 7.49-7.51 (m, 2H), 7.34-7.35 (m, 2H).

Workup

  1. customprepared
  2. additionwas added over 3 min
  3. customSolvent was removed under vacuum
  4. temperaturethe resulting suspension was cooled to an ice bath
  5. additionIce water (300 mL) was added
  6. stirringby stirring for 1 h
  7. filtrationThe product was collected by filtration
  8. washwashed with 0.1 M aqueous HCl (50 mL×2)
  9. customAfter drying under vacuum at 50° C. for 2 d

Sources & evidence

ORD record
ord-5543b71ab48e46f3a195219e8437d393
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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