Dimethyl Sulfoxide → HCID 22145688, compound

HRID 1994356Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[N:14]=[N:15][C:16]([CH2:21][OH:22])=[CH:17][C:18]=1[O:19][CH3:20].C(N(CC)CC)C>ClCCl.O>[CH3:20][O:19][C:18]1[CH:17]=[C:16]([CH:21]=[O:22])[N:15]=[N:14][C:13]=1[O:12][CH3:11]

Participants

Conditions

Temperature: -60 °C

Procedure

A solution of oxalyl chloride (0.61 mL) in dichloromethane (11 mL) is cooled to −60° C. and dimethylsulphoxide (0.98 g) is added dropwise maintaining the reaction mixture at −60° C. After 15 minutes a solution of 3,4-dimethoxy-6-hydroxymethylpyridazine (1.0 g) in dichloromethane (42 mL) is added dropwise during 45 minutes maintaining the reaction mixture at −60° C. After a further 15 minutes triethylamine (3.96 mL) is added, the mixture stirred at −60° C. for 15 minutes then cooling is discontinued. When the reaction mixture attains room temperature stirring is continued for 1 hour. The reaction mixture is diluted with water (100 mL) and dichloromethane (100 mL) and the organic phase separated. The aqueous phase is re-extracted with dichloromethane (100 mL) and the combined extracts are dried (MgSO4). Evaporation gave 5,6-dimethoxypyridazine-3-carboxaldehyde (0.95 g) as a white solid, m.p. 179-81° C.

Workup

temperaturemaintaining the reaction mixture at −60° C
temperaturethen cooling
stirringWhen the reaction mixture attains room temperature stirring
waitis continued for 1 hour
customthe organic phase separated
extractionThe aqueous phase is re-extracted with dichloromethane (100 mL)
dry with materialthe combined extracts are dried (MgSO4)
customEvaporation

Sources & evidence

ORD record: ord-ee3c4138c74a4dd4a62dabb0736c9f5c
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652144B2

Reaction notes

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