Lawesson's reagent → 1-(Pyridazin-3-yl)ethan-1-ol

HRID 1503430Notes

Reaction equation

HRID 1503430 reaction equation
CON(C)[C:4]([C:6]1[N:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5].[CH3:13]OC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH:4]([OH:5])[CH3:13])[N:7]=1

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 58197546N-methoxy-N-methylpyridazine-3-carboxamide

Product 1

HCID 151975111-(Pyridazin-3-yl)ethan-1-olYield 157.4%

Procedure

According to a similar synthesis of compound 4 described in Example 346, compound 1 (500 mg, 1.17 mmol) was alkylated with 1-Bromo-2-methoxy-ethane (180 mg, 1.3 mmol) to give compound 2 (360 mg, 65%) as a white solid. Compound 2 (200 mg, 0.43 mmol) was reacted with Lawesson's Reagent (190 mg, 0.47 mmol) to give compound 3 (84 mg, 50%) as a white solid. And compound 3 (80 mg, 0.17 mmol) was converted to hydantoin 4 (55 mg, 70%) as a white solid.

Sources & evidence

ORD record
ord-5a8201ebf0a646d68d9352fd16f5d4ec
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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