Triethylamine → 4-(4-Fluoro-3-isocyanato-benzyl)-2H-phthalazin-1-one

HRID 600260

Reaction equation

HRID 600260 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[F:20])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[NH:8][N:7]=1.C(N(CC)CC)C.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[F:20][C:19]1[CH:18]=[CH:17][C:4]([CH2:5][C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[NH:8][N:7]=2)=[CH:3][C:2]=1[N:1]=[C:29]=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 184443734-(3-amino-4-fluorobenzyl)-2H-phthalazin-1-one

Product 1

HCID 598565454-(4-Fluoro-3-isocyanato-benzyl)-2H-phthalazin-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-(3-amino-4-fluoro-benzyl)-2H-phthalazin-1-one (1)(4.0 g, 14.8 mmol) in anhydrous DCM (1.6 L) and triethylamine (4.62 mL, 40.86 mmol), was added a dropwise preformed solution of triphosgene (2.75 g, 9.28 mmol) in anhydrous DCM (327 mL) and stirred for 70 minutes and 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=4.49 mins, (M+MeOH) 328.0.

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-78509e2f26d7418f81df896423ac6f67
Source dataset
uspto-grants-2011_03
Patent number
US07902193B2

Linked notes

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