Triethylamine → 4-(4-Isocyanato-pyridin-2-ylmethyl)-2H-phthalazin-1-one

HRID 600267Notes

Reaction equation

HRID 600267 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[NH:11][N:10]=2)[CH:3]=1.C(N(CC)CC)C.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[N:1]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[NH:11][N:10]=2)[CH:3]=1)=[C:28]=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 598565694-(4-Amino-pyridin-2-ylmethyl)-2H-phthalazin-1-one

Product 1

HCID 598565814-(4-Isocyanato-pyridin-2-ylmethyl)-2H-phthalazin-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-(4-amino-pyridin-2-ylmethyl)-2H-phthalazin-1-one (21) (0.40 g, 1.48 mmol) in anhydrous DCM (160 mL) and triethylamine (0.46 mL, 4.09 mmol), was added a dropwise preformed solution of triphosgene (0.27 g, 0.93 mmol) in anhydrous DCM (30 mL). The reaction was stirred for 6 hrs at room temperature. The reaction mixture was then concentrated to dryness in vacuo yielding a grey solid. Single peak in LC-MS analysis, (yield taken to be quantitative) no purification performed. m/z (LC-MS, ESP), RT=3.79 mins, (M+MeOH) 329.0.

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness in vacuo
  2. customyielding a grey solid
  3. customSingle peak in LC-MS analysis, (yield taken to be quantitative)
  4. customno purification

Sources & evidence

ORD record
ord-06b6ab4d05a84e5a9d9cbbdcee8fc53f
Source dataset
uspto-grants-2011_03
Patent number
US07902193B2

Reaction notes

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