Phenylacetyl chloride → N-(6-chloropyridazin-3-yl)-2-phenylacetamide

HRID 538092Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[C:9]1([CH2:15][C:16](Cl)=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN1C(=O)CCC1>[Cl:8][C:5]1[N:4]=[N:3][C:2]([NH:1][C:16](=[O:17])[CH2:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 19 °C

Procedure

To a solution of 3-amino-6-chloropyridazine (11.14 g, 86.0 mmol) in NMP (279 mL) at 19° C. was added phenylacetyl chloride (18.2 mL, 137.6 mmol) dropwise over 5 minutes with the internal temperature of the solution maintained Ti≦28° C. The resulting mixture was stirred at 19° C. for 90 minutes and poured into ice water (557 mL). The white precipitate was collected by suction filtration, rinsed with water (2×110 mL) and diethyl ether (110 mL). The product was dried overnight under high vacuum to afford N-(6-chloropyridazin-3-yl)-2-phenylacetamide (xxx, 18.8 g). 1H NMR (300 MHz, DMSO-d6) δ 11.57 (s, 1H), 8.40 (d, J=9.636 Hz, 1H), 7.90 (d, J=9.516 Hz, 1H), 7.36 (m, 5H) 3.82 (s, 2H)

Workup

temperaturemaintained Ti
custom≦28° C
filtrationThe white precipitate was collected by suction filtration
washrinsed with water (2×110 mL) and diethyl ether (110 mL)
customThe product was dried overnight under high vacuum

Sources & evidence

ORD record: ord-52a8e7c95e6b4327be9057599a8c7479
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865718B2

Reaction notes

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