Thiophosgene → HCID 86683464, compound

HRID 515789Notes

Reaction equation

HRID 515789 reaction equation
[C:1](Cl)(Cl)=[S:2].[F:5][C:6]([F:18])([F:17])[C:7]1[N:11]2[N:12]=[C:13]([NH2:16])[CH:14]=[CH:15][C:10]2=[N:9][N:8]=1>N1C=CC=CC=1.C1COCC1>[N:16]([C:13]1[CH:14]=[CH:15][C:10]2[N:11]([C:7]([C:6]([F:18])([F:17])[F:5])=[N:8][N:9]=2)[N:12]=1)=[C:1]=[S:2]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 4915708889943-49-1

Product 1

HCID 86683464HCID 86683464, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Thiophosgene (1 mL, 12.7 mmol) was added to a solution of 3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine (860 mg, 4.23 mmol) in pyridine (10 mL) and THF (15 mL) and the resulting dark mixture was stirred at room temperature for 2 h. The dark mixture was partitioned between EtOAc and 1M HCl. The organic layer was washed with 1M HCl (2×), dried over sodium sulfate, and evaporated to dryness to afford 545 mg (60% pure) of 6-isothiocyanato-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine as a dark purple solid. LCMS [M+1]+ 278.5 (OMe adduct).

Workup

  1. customThe dark mixture was partitioned between EtOAc and 1M HCl
  2. washThe organic layer was washed with 1M HCl (2×)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-66f7e34e6099439c82477236748c65cb
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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